2024-03-28T11:13:31Zhttp://uvadoc.uva.es/oai/requestoai:uvadoc.uva.es:10324/214432021-06-23T11:57:02Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
Andrés García, José María
Ceballos, Miriam
Maestro Fernández, Alicia
Sanz, Isabel
Pedrosa Sáez, Rafael
Catalizadores
Producción Científica
The catalytic activity of different supported bifunctional thioureas on sulfonylpolystyrene resins has been studied in the nitro-
Michael addition of different nucleophiles to trans-β-nitrostyrene derivatives. The activity of the catalysts depends on the length of
the tether linking the chiral thiourea to the polymer. The best results were obtained with the thiourea derived from (L)-valine and
1,6-hexanediamine. The catalysts can be used in only 2 mol % loading, and reused for at least four cycles in neat conditions. The
ball milling promoted additions also worked very well.
Ministerio de Economía, Industria y Competitividad (CTQ2014-59870-P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
2016-12-05T10:41:25Z
2016-12-05T10:41:25Z
2016
info:eu-repo/semantics/article
Beilstein Journal of Organic Chemistry, 2016, 12, p. 628–635
1860-5397
http://uvadoc.uva.es/handle/10324/21443
10.3762/bjoc.12.61
628
12
635
Beilstein Journal of Organic Chemistry
eng
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Beilstein-Institut
https://uvadoc.uva.es/bitstream/10324/21443/6/Beilstein-J-Org-Chem-2016.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21443
oai:uvadoc.uva.es:10324/214442021-06-23T11:57:03Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Short Synthesis of Novel Recyclable Chiral Bifunctional Thioureas from Aminoalkyl Polystyrene and their use as Organocatalysts in Stereoselective aza-Henry Reaction
Andrés García, José María
Maestro Fernández, Alicia
Rodríguez Ferrer, Patricia
Simón de la Fuente, Inmaculada
Pedrosa Sáez, Rafael
Catalizadores
Producción Científica
A series of supported bifunctional thioureas has been prepared, in one or two steps, from commercially available aminoalkyl polystyrene resins. They differ in the length of the tether attaching the thiourea to the polymer chain, and the nature of the amino thiourea component. All the materials are able to promote stereoselective aza-Henry reaction with very good stereoselection, and they can be recycled maintaining the catalytic activity.
Ministerio de Economía, Industria y Competitividad (CTQ2014-59870-P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
2016-12-05T10:59:21Z
2016-12-05T10:59:21Z
2016
info:eu-repo/semantics/article
ChemistrySelect, vol.1, Issue 15, September 16, 2016, p. 5057–5061
2365-6549
http://uvadoc.uva.es/handle/10324/21444
10.1002/slct.201601213
5057
15
5061
ChemistrySelect
1
eng
http://onlinelibrary.wiley.com/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Wiley
https://uvadoc.uva.es/bitstream/10324/21444/6/ChemistrySelect-2016.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21444
oai:uvadoc.uva.es:10324/214452021-06-24T07:42:26Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Bottom-up Synthesis of Novel Supported Thioureas and Their Use in Enantioselective Solvent-free Aza-Henry and Michael Additions
Andrés García, José María
Cruz Ruiz, Noelia de la
Valle Álvarez, María
Pedrosa Sáez, Rafael
Química orgánica
Producción Científica
Two sets of supported chiral thioureas, which differ in the length of the tether connecting the chiral appendage to the polymer structure and the effective functionalization, have been prepared by co-polymerization of styrene, novel styryl thioureas derived from (L)-valine, and divinylbenzene. The efficiency of these polymeric thioureas has been tested in two different enantioselective transformations such as aza-Henry and nitro-Michael reactions in neat reaction conditions. The obtained results show that it is possible to recycle, and they are able to promote the reactions with good enantioselectivity in low catalyst loading.
Ministerio de Economía, Industria y Competitividad (CTQ2014-59870-P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
2016-12-05T11:42:38Z
2016-12-05T11:42:38Z
2016
info:eu-repo/semantics/article
ChemPlusChem, vol. 81, Issue 1, January 2016, p. 86–92
2192-6506
http://uvadoc.uva.es/handle/10324/21445
10.1002/cplu.201500476
86
1
92
ChemPlusChem
81
eng
http://onlinelibrary.wiley.com/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
Wiley Online Library
application/pdf
Wiley-VCH Verlag
Wiley Online Library
https://uvadoc.uva.es/bitstream/10324/21445/6/ChemPlusChem-2016-81.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21445
oai:uvadoc.uva.es:10324/214462021-06-24T07:42:25Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Organocatalytic Domino Michael-Heterocyclization Reaction of Unsaturated Aldehydes and Cyano Ketones. Synthesis of Enantioenriched 4,5,6-Trisubstituted 3,4-Dihydropyranones
Guevara Pulido, James Oswaldo
Andrés García, José María
Pedrosa Sáez, Rafael
Química orgánica
Producción Científica
α,β-Unsaturated aldehydes with aliphatic, electron-poor aromatic, or electron-withdrawing substituents at the β position easily react with different ketones leading to enantioenriched hemiacetals, which were further oxidized to give 4,5,6-trisubstituted-3,4-dihydropyranones in good yields and with excellent enantioselectivities. The behavior of the ketones is dependent on the α substituent of the carbonyl group, and a fine-tuning of the pKa values is necessary to obtain good results.
Ministerio de Economía, Industria y Competitividad (CTQ2011-28487)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Universidad de Valladolid for a pre-doctoral fellowships
2016-12-05T12:01:25Z
2016-12-05T12:01:25Z
2014
info:eu-repo/semantics/article
European Journal of Organic Chemistry, 2014, Volume 2014, Issue 36, p. 8072–8076
1434-193X
http://uvadoc.uva.es/handle/10324/21446
10.1002/ejoc.201402982
8072
36
8076
European Journal of Organic Chemistry
2014
eng
http://onlinelibrary.wiley.com/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Wiley
https://uvadoc.uva.es/bitstream/10324/21446/6/Eur-J-Org-Chem-2014-8072.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21446
oai:uvadoc.uva.es:10324/214472021-06-24T07:42:25Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Chiral Ureas and Thioureas Supported on Polystyrene for Enantioselective Aza-Henry Reaction in Solvent-free conditions
Pedrosa Sáez, Rafael
Andrés García, José María
Ávila, Deisy P.
Ceballos, Miriam
Pindado Hernández, Rodrigo
Catalizadores
Química orgánica
Producción Científica
Novel bifunctional ureas and thioureas inmovilized on sulfonylpystyrene have been prepared as recoverable and reusable organocatalysts and used in the stereoselective aza-Henry reaction under solvent-free conditions. The activity and stereoselection of the catalysts are dependent on the length of the tether bringing the active site and the polymer, being the catalyst derived from 1,6-hexane diamine the best one. It has been also demonstrated that the supported catalysts are more effective than the homologous soluble catalysts.
Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
2016-12-05T12:18:32Z
2016-12-05T12:18:32Z
2015
info:eu-repo/semantics/article
Green Chemistry, 2015, vol.17, p. 2217-2225
1463-9262
http://uvadoc.uva.es/handle/10324/21447
10.1039/C4GC02474E
2217
17
2225
Green Chemistry
eng
http://pubs.rsc.org/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/21447/6/Green-Chem-2015-17.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21447
oai:uvadoc.uva.es:10324/214482021-06-24T07:42:24Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
One-pot Sequential Organocatalytic Michael-Tishchenko-Lactonization Reactions. Synthesis of Enantioenriched 4, 5, 6 -Trisubstituted - Lactones
Guevara Pulido, James Oswaldo
Andrés García, José María
Pedrosa Sáez, Rafael
Catalizadores
Química orgánica
Producción Científica
Enantioenriched trisubstituted lactones were obtained in good yields and moderate to very good enantioselectivities in one-pot process, which implies a sequential organocatalyzed Michael addition of ketones to enals, followed by catalytic intramolecular diastereoselective Tishchenko reaction and lactonization. The final lactones were obtained as single diastereoisomers, demonstrating that the mixture of the anti and syn diastereomers epimerized to the syn hydroxy ester during the oxido-reduction step.
Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Universidad de Valladolid for a pre-doctoral fellowships
2016-12-05T12:44:49Z
2016-12-05T12:44:49Z
2014
info:eu-repo/semantics/article
Journal of Organic Chemistry, 2014, 79(18), p. 8638-8644
0022-3263
http://uvadoc.uva.es/handle/10324/21448
10.1021/jo5013724
8638
18
8644
Journal of Organic Chemistry
79
eng
http://pubs.acs.org/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
American Chemical Society
https://uvadoc.uva.es/bitstream/10324/21448/7/J-ORG-CHEM-2014-79-8638.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21448
oai:uvadoc.uva.es:10324/214492021-06-24T07:42:23Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Tandem Diastereo- and Enantioselective Preparation of Aryl and Alkyl Cyclopropyl Carbinols with Three Adjacent Stereocenters Using Perhydrobenzoxazines and Diethylzinc
Infante Blanco, Rebeca
Nieto Román, Francisco Javier
Andrés Juan, Celia
Química orgánica
Producción Científica
The enantio‐ and diastereoselective one‐pot ethylation/cyclopropanation is efficiently promoted by a chiral perhydrobenzoxazine. The catalytic system tolerates a wide range of di‐ and trisubstituted α,β‐unsaturated aldehydes and has been found to be highly diastereo- and enantioselective. Enals leading to intermediates lacking allylic strain or with either A1,2 or A1,3 strain afford the corresponding syn hydroxycyclopropanes very selectively. While α‐methyl enals are successfully ethylated/cyclopropanated, the presence of bulky substituents at alpha position of the enal constitutes a limitation to the substrate scope. The use of 1,1‐diiodoethane allows the obtention of the corresponding enantioenriched cyclopropylcarbinol, which bears carbon‐substituents at all three positions of the ring, with good enantiocontrol, although moderate diastereoselectivity. A procedure for the asymmetric one‐pot arylation/cyclopropanation of enals is proposed, which involves the use of triarylboroxin, diethylzinc and diiodomethane.
Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Universidad de Valladolid for a pre-doctoral fellowships
2016-12-05T13:05:23Z
2016-12-05T13:05:23Z
2014
info:eu-repo/semantics/article
Organic & Biomolecular Chemistry, 2014, 12, p. 345-354
1477-0520
http://uvadoc.uva.es/handle/10324/21449
10.1039/C3OB41797B
345
12
354
Organic & Biomolecular Chemistry
eng
http://pubs.rsc.org/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/21449/6/Org-Biomol-Chem-2014.12.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21449
oai:uvadoc.uva.es:10324/214502021-06-24T07:42:22Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
7-Endo selenocyclization reactions on chiral 3-prenyl and 3-cinnamyl-2 hydroxymethylperhydro-1,3-benzoxazine derivatives. A way to enantiopure 1,4-oxazepanes
Nieto Román, Francisco Javier
Andrés Juan, Celia
Pérez Encabo, Alfonso
Química orgánica
Producción Científica
Enantiopure 1,4-oxazepanes derivatives have been prepared by selenocyclofunctionalization of chiral 3-prenyl- and 3-cinnamyl-2-hydroxymethyl-substituted perhydro-1,3-benzoxazine derivatives. The 7-endo-cyclization occurs in high yields and diastereoselection. The regio and stereochemistry of the cyclization products was dependent of the substitution pattern of the double bond, the nature of the hydroxyl group and the experimental conditions.
Ministerio de Economía, Industria y Competitividad (CTQ2014-59870-P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Thanks to Dr. José M. Martín-Álvarez for his assistance in the determination of the X-ray structures
2016-12-05T13:18:01Z
2016-12-05T13:18:01Z
2015
info:eu-repo/semantics/article
Organic & Biomolecular Chemistry, 2015,13, p. 9118-9126
1477-0520
http://uvadoc.uva.es/handle/10324/21450
10.1039/C5OB01297J
9118
13
9126
Organic & Biomolecular Chemistry
eng
http://pubs.rsc.org/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/21450/6/Org-Biomol-Chem-2015-13.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21450
oai:uvadoc.uva.es:10324/214512021-06-24T07:42:21Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone
Guevara Pulido, James Oswaldo
Andrés García, José María
Pedrosa Sáez, Rafael
Química orgánica
Producción Científica
The reaction of enals with α,α′-diaryl-substituted acetones (pKa > 18) catalyzed by (S)-1-(2-pyrrolidinylmethyl) pyrrolidine provides direct access to enantioenriched 2,5,6-trisubstituted-3-hydroxy cyclohexanones. The process constitutes a highly stereoselective organocatalytic tandem Michael-intramolecular aldol reaction. It has been demonstrated that the stereoselection is dependent on the reaction conditions because only syn diastereoisomers are able to cyclize, and that anti diastereoisomers participate in a retro-Michael process decreasing the enantioselection.
Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Universidad de Valladolid for a pre-doctoral fellowships
2016-12-05T13:32:46Z
2016-12-05T13:32:46Z
2015
info:eu-repo/semantics/article
RSC Advances, 2015, 5, p. 65975-65981
2046-2069
http://uvadoc.uva.es/handle/10324/21451
10.1039/C5RA11215J
65975
5
65981
RSC Advances
eng
http://pubs.rsc.org/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/21451/6/RSC-Adv-2015-5.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21451
oai:uvadoc.uva.es:10324/214522021-06-24T07:42:20Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Enantioselective Synthesis of Seven-Membered Carbo- and Heterocyles by Organocatalyzed Intramolecular Michael Addition
Guevara Pulido, James Oswaldo
Andrés García, José María
Ávila, Deisy P.
Pedrosa Sáez, Rafael
Química orgánica
Producción Científica
Unprecedented diastereo- and enantioselective synthesis of seven-membered rings has been achieved by organocatalyzed intramolecular Michael addition of enals bearing β-diketone functionality. The cyclization leads to 2,3-disubstituted cycloheptanone derivatives in high yield and excellent stereoselectivity. The same organocatalyzed cyclization process has been used to prepare six-membered homologs, but with lower stereoselectivity.
Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Universidad de Valladolid for a pre-doctoral fellowships
2016-12-05T13:48:27Z
2016-12-05T13:48:27Z
2016
info:eu-repo/semantics/article
RSC Advances, 2016, 6, p. 30166-30169
http://uvadoc.uva.es/handle/10324/21452
10.1039/C6RA04198A
30166
6
30169
RSC Advances
eng
http://pubs.rsc.org/
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/21452/6/RSC-Adv-2016-6.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/21452
oai:uvadoc.uva.es:10324/289472021-06-24T07:42:18Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Recyclable Chiral Bifunctional Thioureas Derived from [60]Fullerene and Their Use as Highly Efficient Organocatalysts for the Asymmetric Nitro-Michael Reaction
Andrés García, José María
González Pérez, Miguel
Maestro Fernández, Alicia
Naharro, Daniel
Pedrosa Sáez, Rafael
Catálisis
Química orgánica
Producción Científica
Three novel fullerothioureas derived from natural valine, phenylalanine, and tert-leucine have been prepared by Prato's reaction of [60]fullerene and the corresponding aldehydes. These hybrids have been used as organocatalysts in a typical stereoselective nitro-Michael addition reaction under homogeneous and neat conditions. The catalysts are easily recoverable by filtration, and are recyclable for at least five times. The addition products were obtained in excellent yields and stereoselectivities by using catalyst loadings of as low as 0.5 mol-%.
2018-07-07
Ministerio de Economía, Industria y Competitividad (Project CTQ2014-59870-P)
2018-03-12T10:18:36Z
2018-07-07T23:40:45Z
2017
info:eu-repo/semantics/article
European Journal of Organic Chemistry, 2017, Volume 2017, Issue 19, Pages 2683–2691
1434-193X
http://uvadoc.uva.es/handle/10324/28947
10.1002/ejoc.201601640
eng
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201601640/full
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Wiley
https://uvadoc.uva.es/bitstream/10324/28947/6/Recyclable-Eur-J-Org-Chem-2017-postprint.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/28947
oai:uvadoc.uva.es:10324/289492021-06-24T07:42:17Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Biodegradable Chitosan-Derived Thioureas as Recoverable Supported Organocatalysts – Application to the Stereoselective Aza-Henry Reaction
Andrés García, José María
González Pérez, Fernando
Maestro Fernández, Alicia
Pedrosa Sáez, Rafael
Valle Álvarez, María
Catálisis
Química orgánica
Producción Científica
Eight different biodegradable chitosan-supported bifunctional chiral thioureas have been prepared as a greener and more sustainable alternative to those supported on petrochemical-derived polymers. These organocatalysts promoted an enantioselective aza-Henry reaction, which afforded good product yields with moderate to high enantioselectivity. The activity and stereodirecting ability of these materials were dependent on the accessibility of the reactants to the active site and increased with the length of the tether that connected the thiourea to the biopolymer. The best performing catalyst was able to be recovered and recycled five times without a loss of activity.
2018-10-10
Ministerio de Economía, Industria y Competitividad (Project CTQ 2014-59870-P)
2018-03-12T10:45:41Z
2018-10-10T23:40:32Z
2017
info:eu-repo/semantics/article
European Journal of Organic Chemistry, 2017, Volume 2017, Issue 25, Pages 3658–3665
http://uvadoc.uva.es/handle/10324/28949
10.1002/ejoc.201700582
eng
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201700582/full
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
Wiley
https://uvadoc.uva.es/bitstream/10324/28949/6/Biodegradable-Eur-J-Org-Chem-2017-postprint.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/28949
oai:uvadoc.uva.es:10324/289502021-06-24T07:42:16Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Supported and Unsupported Chiral Squaramides as Organocatalysts for Stereoselective Michael Additions: Synthesis of Enantiopure Chromenes and Spirochromanes
Andrés García, José María
Losada, Jorge
Maestro Fernández, Alicia
Rodríguez Ferrer, Patricia
Pedrosa Sáez, Rafael
Catálisis
Química orgánica
Producción Científica
Novel supported chiral bifunctional squaramides have been easily prepared starting from diamines derived from natural amino acids and commercially available aminoalkyl polystyrene resins. These squaramides behave as excellent stereoselective recoverable organocatalysts in different Michael additions, in neat conditions at room temperature. The reaction on 2-(2-nitrovinyl) phenol as electrophile lead, in excellent yields and enantioselectivities, to intermediates that can be easily transformed into 4H-chromenes, and spirochromanones.
2018-10-10
Ministerio de Economía, Industria y Competitividad - FEDER (Proyect CTQ2014-59870-P)
2018-03-12T11:00:17Z
2018-10-10T23:40:32Z
2017
info:eu-repo/semantics/article
Journal of Organic Chemistry, 2017, Volume 82, Issue16, Pages 8444-8454
0022-3263
http://uvadoc.uva.es/handle/10324/28950
10.1021/acs.joc.7b01177
eng
https://pubs.acs.org/doi/full/10.1021/acs.joc.7b01177
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
American Chemical Society
https://uvadoc.uva.es/bitstream/10324/28950/6/Supported-J-Org-Chem-2017-postprint.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/28950
oai:uvadoc.uva.es:10324/289512021-06-24T07:42:19Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Dimethylzinc-Mediated Addition of Phenylacetylene to α-Diketones Catalyzed by Chiral Perhydro-1,3-benzoxazines
Infante Blanco, Rebeca
Martín Álvarez, José Miguel
Andrés Juan, Celia
Nieto Román, Francisco Javier
Producción Científica
An efficient enantioselective Me2Zn-mediated mono addition of phenylacetylene to α-diketones in the presence of a chiral perhydro-1,3-benzoxazine ligand is described. At temperatures higher than -20 ºC a kinetic resolution of the resulting α-hydroxy ketone occurs which greatly improves the enantioselectivity although with moderate chemical yield. The alkynylation of nonsymmetrical aromatic diketones with electronically different substituents on the aromatic rings proceed with high regioselectivity. This procedure allows the preparation of α-hydroxy-α-ynyl-ketones as highly enantioenriched materials.
2018-07-07
Ministerio de Economía, Industria y Competitividad (Project CTQ2014-59870 P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
2018-03-12T12:08:35Z
2018-07-07T23:40:44Z
2017
info:eu-repo/semantics/article
Organic Letters, 2017, 19 (7), pp 1516–1519
1523-7060
http://uvadoc.uva.es/handle/10324/28951
10.1021/acs.orglett.7b00252
eng
https://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b00252
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
American Chemical Society
https://uvadoc.uva.es/bitstream/10324/28951/6/Dimethylzinc-Org-Lett-2017-postprint.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/28951
oai:uvadoc.uva.es:10324/323702021-06-24T07:42:36Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Chiral Bifunctional Thioureas and Squaramides and Their Copolymers as Recoverable Organocatalysts. Stereoselective Synthesis of 2-Substituted 4-Amino-3-nitrobenzopyrans and 3-Functionalized 3,4-Diamino-4H-Chromenes
Andrés García, José María
Maestro Fernández, Alicia
Valle Álvarez, María
Pedrosa Sáez, Rafael
Aminobenzopiranos
Aminobenzopyranes
Producción Científica
Novel styryl-substituted thioureas and squaramides were obtained in three steps from commercially available 4-hydroxy-3,5-dichloroaniline. These organocatalysts promote cascade reactions in high yields and excellent stereoselection. By using only a 5 mol % loading of catalyst, it is possible to obtain 2,3,4-trisubstituted benzopyrans by reaction of α-amido sulfones derived from salicyladehydes and nitrostyrenes or 2,3,4-trisubstituted 4H-chromenes by reaction of the same α-amido sulfones with (phenylsulfonyl)acetonitrile in excellent diastereo- and enantioselectivities. Two polymeric thioureas and squaramides were prepared by copolymerization of the best monomeric catalysts with styrene and divinylbenzene and used for the same transformations. These polymers behave also as excellent stereoselective catalysts that can be recovered and reused for five cycles.
2019-11-11
2019-11-11
Ministerio de Economía, Industria y Competitividad (Project FEDER-CTQ2014-59870-P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación - Project FEDER-VA115P17)
2018-10-29T13:49:37Z
2018
info:eu-repo/semantics/article
Journal of Organic Chemistry, 2018, 83 (10), pp 5546–5557
0022-3263
http://uvadoc.uva.es/handle/10324/32370
https://doi.org/10.1021/acs.joc.8b00567
eng
https://pubs.acs.org/doi/10.1021/acs.joc.8b00567
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
American Chemical Society
https://uvadoc.uva.es/bitstream/10324/32370/6/Chiral-Bifunctional-Thioureas-Postprint.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/32370
oai:uvadoc.uva.es:10324/334192021-06-24T07:42:41Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Diastereo- and Enantioselective Syntheses of Trisubstituted Benzopyrans by Cascade Reactions Catalyzed by Monomeric and Polymeric Recoverable Bifunctional Thioureas and Squaramides
Andrés García, José María
Maestro Fernández, Alicia
Valle Álvarez, María
Valencia, Isabel
Pedrosa Sáez, Rafael
Catalizadores
Gestión de residuos
Catalysts
Waste management
Producción Científica
4-Vinylphenyl-substituted squaramides have been tested as organocatalysts for the diastereo- and enantioselective synthesis of trisubstituted benzopyrans via an oxa-Michael intramolecular nitro-Michael cascade reaction. Both the enantio- and diastereoselection were good to moderate, depending on the nature of the chiral scaffold in the catalyst. The diastereoselection is better for the most active catalyst because the final products epimerize at C-3 along the time. Supported squaramide sq-9 prepared by copolymerization of sq-4 with styrene and divinylbenzene is also effective in promoting the cascade reaction, and it is recoverable and reusable for five cycles maintaining the activity.
Ministerio de Economía, Industria y Competitividad (Project FEDER-CTQ2014-59870-P)
Junta de Castilla y León (Projects FEDER-VA115P17 and VA149G18)
2018-12-12T09:56:17Z
2018-12-12T09:56:17Z
2018
info:eu-repo/semantics/article
ACS Omega, 2018, 3 (12), pp 16591–16600
2470-1343
http://uvadoc.uva.es/handle/10324/33419
https://doi.org/10.1021/acsomega.8b02302
eng
https://pubs.acs.org/doi/10.1021/acsomega.8b02302
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
American Chemical Society
https://uvadoc.uva.es/bitstream/10324/33419/6/ACS-Omega2018-3-16591%e2%88%9216600.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/33419
oai:uvadoc.uva.es:10324/339172021-06-24T07:42:39Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Chiral Bifunctional Thioureas and Squaramides Grafted into Old Polymers of Intrinsic Microporosity for Novel Applications
Valle Álvarez, María
Martín, Laura
Maestro Fernández, Alicia
Andrés García, José María
Pedrosa Sáez, Rafael
Organocatálisis
Organocatalysis
Polímeros de microporosidad
Polymers of microporosity
Producción Científica
We have prepared different polymeric chiral bifunctional thioureas and squaramides by modification of the very well-known polymers of intrinsic microporosity (PIM), specifically PIM-1 and PIM-CO-1, to be used as recoverable organocatalysts. The installation of the chiral structures into the polymers has been done in two or three steps in high yields. The catalytic activity of the resulting materials has been proved in the stereoselective nitro-Michael addition and in a cascade process, which allows the synthesis of enantioenriched 4H-chromene derivatives. Squaramide II and thiourea III have been used in six cycles maintaining their activity. View Full-Text
Ministerio de Economía, Industria y Competitividad - FEDER (Project CTQ2014-59870-P)
Junta de Castilla y León - FEDER (programa de apoyo a proyectos de investigación - Ref. VA115P17, and VA149G18)
2019-01-11T12:01:32Z
2019-01-11T12:01:32Z
2019
info:eu-repo/semantics/article
Polymers 2019, 11(1), 13
2073-4360
http://uvadoc.uva.es/handle/10324/33917
https://doi.org/10.3390/polym11010013
eng
https://www.mdpi.com/2073-4360/11/1/13
Attribution-NonCommercial-NoDerivatives 4.0 International
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/33917/6/polymers-11-00013-v2-1.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/33917
oai:uvadoc.uva.es:10324/372732021-11-18T09:27:56Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
A note on the combustion of blends of diesel and soya, sunflower and rapeseed vegetable oils in a light boiler
San José Alonso, Julio Francisco
López Sastre, Juan Antonio
Romero Ávila, C.
López, E.
Combustion mixtures, diesel, sunflower oil, rape oil, soya oil
Producción Científica
This paper deals with the study of the vegetable oils (VO) used as fuel for heating. The properties of sunflower, rape and soya oils are studied and these are compared with the properties of C-diesel fuel (used for heating domestic purposes in Spain). The mixtures of VO and diesel are studied and characterized and, finally, the results of a series of combustion trials of the mixtures in a conventional heating installation with a mechanical pulverization burner are presented. The results show that viscosity of VO limits the use of blends up to 40% of them, and the oxygen present in their structures contributes to an efficiency gain
2019-07-24T17:17:34Z
2019-07-24T17:17:34Z
2008
info:eu-repo/semantics/article
info:eu-repo/semantics/submittedVersion
Biomass and Bioenergy, 2008, vol. 32, p. 880-886
0961-9534
http://uvadoc.uva.es/handle/10324/37273
10.1016/j.biombioe.2008.01.007
880
9
886
Biomass and Bioenergy
32
eng
https://www.journals.elsevier.com/biomass-and-bioenergy/editorial-board
info:eu-repo/semantics/restrictedAccess
ScienceDirect Elsevier
application/pdf
ScienceDirect Elsevier
https://uvadoc.uva.es/bitstream/10324/37273/3/Article-1_biomass.pdf.jpg
Hispana
TEXT
http://rightsstatements.org/vocab/CNE/1.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/37273
oai:uvadoc.uva.es:10324/372752021-11-17T08:47:52Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Combustion of Soya Oil and Diesel Oil Mixtures for Use in Thermal Energy Production
San José Alonso, Julio Francisco
López Sastre, Juan Antonio
Rodríguez Duque, E.
López Romero-Ávila, Enrique José
Romero Ávila, C.
Soya oil, Vegetable oils-Diesel mixtures, Thermal energy.
Producción Científica
In August 2005, Spain approved the Plan for Renewable Energy Sources for the period 2005-2010 (P.E.R.), including co-combustion installations. Co-combustion in the P.E.R. aims to increase power output by 12,185.3 GWh in five years and shows great interest in studies of the combustion of mixtures of fossil and bio-combustible fuels.
This paper presents studies of the co-combustion of soya oil and diesel for thermal heating. The paper begins with a characterization of soya oil as well as mixtures of this oil, with diesel, as fuels. The combustion of the soya oil mixtures and diesel is made in an installation, where the pressure of injection as well as the air volume of the burner can be changed. The obtained results inside to be the environmental average legislation and a greater efficiency of combustion is found. The conclusions show that the use of mixtures of soya oil and Diesel for producing thermal energy in conventional equipment is feasible.
2019-07-25T08:49:31Z
2019-07-25T08:49:31Z
2008
info:eu-repo/semantics/article
info:eu-repo/semantics/draft
Energy & Fuels 2008, 22, 3513-3516
0887-0624
http://uvadoc.uva.es/handle/10324/37275
10.1021/ef800261u
3513
5
3516
Energy & Fuels
22
1520-5029
spa
https://pubs.acs.org/page/enfuem/about.html
info:eu-repo/semantics/restrictedAccess
American Chemical Society
application/pdf
American Chemical Society
https://uvadoc.uva.es/bitstream/10324/37275/4/art%c3%adculo1504081_repositorio_energy%20and%20fuel.pdf.jpg
Hispana
TEXT
http://rightsstatements.org/vocab/CNE/1.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/37275
oai:uvadoc.uva.es:10324/377192021-06-24T07:43:27Zcom_10324_28542com_10324_952com_10324_894com_10324_1187com_10324_931col_10324_28543col_10324_1408
Synthesis of Enantioenriched 3-Amino-3-Substituted Oxindoles by Stereoselective Mannich Reaction Catalyzed by Supported Bifunctional Thioureas
Rodríguez Ferrer, Patricia
Sanz Novo, Miguel
Maestro Fernández, Alicia
Andrés García, José María
Pedrosa Sáez, Rafael
Catálisis asimétrica
Asymmetric catalysis
3-Amino-oxindoles
3-Amino-oxindoles
Pirazoles quirales
Chiral pyrazoles
Tioureas bifuncionales
Bifunctional thioureas
Reacción de Mannich
Mannich reaction
Producción Científica
Enantioenriched 3‐amino‐3‐substituted oxindoles have been obtained by addition of different nucleophiles to N‐Boc ketimines derived from isatin catalyzed by chiral bifunctional supported thioureas. The Mannich reaction occurs with excellent enantioselection, but poor diastereoselection when prochiral nucleophiles were used. The supported catalyst were recovered and reused for five times without loss of activity. The mixture of diastereoisomers formed when a prochiral structure was used as nucleophile was converted into a single enantioenriched pyrazolyl derivative.
Ministerio de Economía, Industria y Competitividad (Project FEDER-CTQ2014–59870-P)
Junta de Castilla y León (Projects FEDER-VA115P17 / VA149G18)
2019-08-30T09:06:30Z
2019-08-30T09:06:30Z
2019
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
Advanced Synthesis and Catalysis, 2019, vol. 361, n. 15. p. 3645-3655
1615-4169
http://uvadoc.uva.es/handle/10324/37719
https://doi.org/10.1002/adsc.201900414
eng
https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201900414
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
© 2019 Wiley-VCH
application/pdf
Wiley Online Library
https://uvadoc.uva.es/bitstream/10324/37719/4/Synthesis-Enantioenriched-ASC-2019.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/37719
oai:uvadoc.uva.es:10324/381032021-06-24T07:43:37Zcom_10324_28542com_10324_952com_10324_894com_10324_1187com_10324_931col_10324_28543col_10324_1408
Synthesis of Enantiopure Oxygen- and Nitrogen-Containing Heterocycles by Diastereoselective Ring-Closing Metathesis Reaction in Perhydro-1,3-benzoxazine Derivatives
Gutiérrez Loriente, Agustín
Martín Álvarez, José Miguel
Prieto, Elena
Andrés Juan, Celia
Nieto Román, Francisco Javier
Síntesis asimétrica
Metátesis
Asymmetric synthesis
Metathesis
Producción Científica
Diastereoselective ring‐closing metathesis reactions on chiral trienic perhydro‐1,3‐benzoxazines derived from (−)‐8‐aminomenthol featuring two diastereotopic olefin chains is described. The diastereochemical outcome of the cyclization appeared to be dependent on the length and position of the olefin chains in perhydro‐1,3‐benzoxazine, the degree of substitution of the double bonds and the ruthenium catalyst used. After separation of the diastereomers, and removal of the chiral auxiliary, enantiopure oxygen‐ and nitrogen‐containing heterocycles were obtained.
Ministerio de Economía, Industria y Competitividad (Project FEDER-CTQ2014-59870-P)
Junta de Castilla y León (Ref. Project FEDER-VA115P17)
2019-09-24T10:35:37Z
2019-09-24T10:35:37Z
2019
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
Advanced Synthesis and Catalysis, Volume361, Issue 5, 2019 Pages 1042-1063
1615-4150
http://uvadoc.uva.es/handle/10324/38103
10.1002/adsc.201801454
1042
5
1063
Advanced Synthesis & Catalysis
361
eng
https://onlinelibrary.wiley.com/doi/10.1002/adsc.201801454
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
© 2019 Wiley
application/pdf
Wiley
https://uvadoc.uva.es/bitstream/10324/38103/4/Synthesis-Enantiopure-Oxygen.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/38103
oai:uvadoc.uva.es:10324/384522021-06-24T07:43:46Zcom_10324_28542com_10324_952com_10324_894com_10324_1187com_10324_931col_10324_28543col_10324_1408
Chiral Bifunctional Thiosquaramides as Organocatalysts in the Synthesis of Enantioenriched 3,3-Disubstituted Oxindoles
Rodríguez Ferrer, Patricia
Naharro, Daniel
Maestro Fernández, Alicia
Andrés García, José María
Pedrosa Sáez, Rafael
Química orgánica
Producción Científica
Four novel chiral bifunctional thiosquaramides have been prepared from cyclopentyl dithiosquarates and diamines derived from natural l‐Valine and l‐tert‐Leucine. The novel thiosquaramides have been tested as organocatalyst in the nitro‐Michael addition of 3‐substituted oxindoles to different β‐aryl‐substituted nitroalkenes. The reaction occurred easily in high yields and excellent stereoselectivities, showing that the novel organocatalysts are much more effective than their thioureas and squaramides homologs.
Junta de Castilla y León (Ref. Project VA115P17)
Junta de Castilla y León (Ref. Project VA149G18)
2019-10-09T08:24:27Z
2019-10-09T08:24:27Z
2019
info:eu-repo/semantics/article
info:eu-repo/semantics/submittedVersion
European Journal of Organic Chemistry 2019, 6539–6549
1434-193X
http://uvadoc.uva.es/handle/10324/38452
10.1002/ejoc.201901327
European Journal of Organic Chemistry
eng
https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201901327
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
© Wiley
application/pdf
Willey
https://uvadoc.uva.es/bitstream/10324/38452/4/Chiral-Bifunctional-.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/38452
oai:uvadoc.uva.es:10324/408852021-06-24T07:43:45Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Supported Bifunctional Chiral Thioureas as Catalysts in the Synthesis of 3‐Amino‐2‐Oxindoles through Enantioselective aza‐Friedel‐Crafts Reaction: Application in Continuous Flow Processes
Rodríguez Rodríguez, Marta
Maestro Fernández, Alicia
Andrés García, José María
Pedrosa Sáez, Rafael
Catálisis asimétrica
Asymmetric catalysis
23 Química
Producción Científica
Supported cinchone‐derived thioureas promote highly enantioselective aza‐Friedel‐Crafts reaction of different naphthols with a variety of N‐Boc ketimines derived from isatin. The catalysts are recoverable and reusable, and one of the supported catalysts has been used in a flow process allowing the synthesis of 3‐amino‐2‐oxindole derivatives in multigram scale with high yield and enantioselectivity.
Junta de Castilla y León (programa de apoyo a proyectos de investigación - Ref. VA115P17)
Junta de Castilla y León (programa de apoyo a proyectos de investigación - Ref. VA149G18)
2020-05-19T11:46:10Z
2020-05-19T11:46:10Z
2020
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
Advanced Synthesis & Catalysis, 2020, 362, 1 –12
1615-4150
http://uvadoc.uva.es/handle/10324/40885
10.1002/adsc.202000238
Advanced Synthesis & Catalysis
1615-4169
eng
https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202000238
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
info:eu-repo/semantics/restrictedAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
© 2020 Wiley-VCH Verlag GmbH
application/pdf
Wiley
https://uvadoc.uva.es/bitstream/10324/40885/5/Supported-bifunctional.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/40885
oai:uvadoc.uva.es:10324/436822021-06-24T07:44:06Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Bifunctional thiourea-modified polymers of intrinsic microporosity for enantioselective α-amination of 3-aryl-2-oxindoles in batch and flow conditions
Martín Maroto, Laura
Maestro Fernández, Alicia
Andrés García, José María
Pedrosa Sáez, Rafael
Polímeros
Polymers
2306 Química Orgánica
Producción Científica
Two novel polymers of intrinsic microporosity decorated with chiral thioureas have been used as recoverable organocatalysts in enantioselective α-amination of 3-aryl-substituted oxindoles, creating a quaternary stereocenter. Both catalysts were able to promote the reaction in excellent yields and good enantioselection. Catalyst II, with a pyridyl nucleus, was used in recycling experiments maintaining the activity without additional reactivation, and in flow processes allowing the synthesis of the amination product in multigram scale.
Junta de Castilla y León (Projects FEDER VA115P17, and VA149G18)
2020-11-25T18:56:16Z
2020-11-25T18:56:16Z
2020
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
Organic and Biomolecular Chemistry, 2020, 18, 9275-9283
1477-0520
http://uvadoc.uva.es/handle/10324/43682
10.1039/D0OB01373K
9275
45
9283
Organic & Biomolecular Chemistry
18
1477-0539
eng
https://pubs.rsc.org/en/content/articlelanding/2020/OB/D0OB01373K#!divAbstract
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
© 2020 Royal Society of Chemistry
application/pdf
Royal Society of Chemistry
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Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
http://uvadoc.uva.es/handle/10324/43682
oai:uvadoc.uva.es:10324/497822021-11-08T21:46:45Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Unexpected domino Silyl-Prins/Aryl migration process from geminal Vinylsilyl alcohols
Díez Poza, Carlos
Barbero Pérez, María Asunción
Alcohols
Alcoholes
Aldehydes
Aldehídos
Genetics
Genética
Cyclization
Ciclización
Producción Científica
The silyl-Prins cyclization of geminal vinylsilyl alcohols and aldehydes, promoted by TMSOTf, provides access to polysubstituted tetrahydropyrans in which the silyl group remains in the molecule and an aryl group has migrated from silicon to carbon. This domino silyl-Prins/aryl migration process is general and high-yielding for aryl, vinyl, or alkyl aldehydes. Moreover, cyclization proceeds with very high stereocontrol in a one-pot reaction in which both quaternary and tertiary stereogenic centers have been created.
Junta de Castilla y León (project VA294P18)
Fondo Social Europeo - Junta de Castilla y León (predoctoral grant Q4718001C)
2021-11-08T12:42:38Z
2021-11-08T12:42:38Z
2021
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Organic Letters, 2021, vol. 23, n. 21. p. 8385-8389
1523-7060
https://uvadoc.uva.es/handle/10324/49782
10.1021/acs.orglett.1c03121
eng
https://pubs.acs.org/doi/10.1021/acs.orglett.1c03121
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2021 The Authors
application/pdf
ACS Publications
https://uvadoc.uva.es/bitstream/10324/49782/4/Unexpected-domino.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/49782
oai:uvadoc.uva.es:10324/507762022-12-04T22:15:28Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
NHC-catalysed [3+2]-asymmetric annulation between pyrazolin-4,5-diones and enals: Synthesis of novel spirocyclic pyrazolone γ-butyrolactones and computational study of mechanism and stereoselectivity
Gil Ordóñez, Marta
Maestro Fernández, Alicia
Ortega, Pablo
Jambrina, Pablo G.
Andrés García, José María
Pyrazolone
Pirazolona
Producción Científica
Chiral pyrazolones with a spirocyclic centre at the C4-position are widely found in a large family of medically relevant compounds. In recent years, organocatalysis, particularly that performed with quiral N-heterocyclic carbenes (NHCs), has allowed the enantioselective synthesis of these spirocyclic compounds despite its inherent difficulty. In this work, we describe the fully diastereo- and highly enantioselective synthesis of novel spirocyclic pyrazolone γ-butyrolactones via NHC-catalysed [3+2] annulation reaction of enals and 1H-pyrazol-4,5-diones. To understand the catalytic mechanism and origin of stereoselectivity, electronic structure calculations were carried out. After considering various pathways, we concluded that stereoselectivity-determining step is the formation of the lactone that proceeds after addition of the NHC derived homoenolate to the electrophilic carbonyl group of pyrazolin-4,5-dione. Our calculations predict that the free energy barrier is lower for the (RS) product, which is also the main product experimentally obtained.
Junta de Castilla y León (projects FEDER-VA115P17 and VA149G18)
Junta de Castilla y León (predoctoral fellowship EDU/556/2019)
Junta de Castilla y León - Fondo Social Europeo (grant EDU/601/2020)
Ministerio de Ciencia, Innovación y Universidades - Agencia Estatal de Investigación - Fundación Salamanca City of Culture and Knowledge (grant PID2020-113147GA-I00)
2021-12-09T12:32:53Z
2021-12-09T12:32:53Z
2022
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
Organic Chemistry Frontiers, 2022, vol. 9, n. 2, p. 420-427
2052-4110
https://uvadoc.uva.es/handle/10324/50776
10.1039/D1QO01462E
eng
https://pubs.rsc.org/en/Content/ArticleLanding/2022/QO/D1QO01462E
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
© 2022 Royal Society of Chemistry
application/pdf
Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/50776/4/NHC-Catalysed-%5b3%2b2%5d-Asymmetric-Annulation.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/50776
oai:uvadoc.uva.es:10324/525322022-07-18T09:32:59Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Synthesis of polysubstituted tetrahydropyrans by stereoselective hydroalkoxylation of silyl alkenols: En route to tetrahydropyranyl marine analogues
Díez Poza, Carlos
Val, Patricia
Pulido Pelaz, Francisco José
Barbero Pérez, María Asunción
Tetrahydropyrans
Acid mediated cyclization
Stereoselective
Marine drugs analogues
23 Química
24 Ciencias de la Vida
Producción Científica
Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated alkenols is described. p-TsOH has shown to be an efficient reagent to yield highly substituted tetrahydropyrans. Moreover, excellent diastereoselectivities are obtained both for unsubstituted and alkylsubstituted vinylsilyl alcohols. The methodology herein developed may potentially be applied to the synthesis of marine drugs derivatives.
Junta de Castilla y León (GR170)
European Social Fund and the Junta de Castilla y León (Grant Q4718001C)
2022-03-17T09:27:38Z
2022-03-17T09:27:38Z
2018
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Marine Drugs, 2018, vol.16, n. 11, p. 421
1660-3397
https://uvadoc.uva.es/handle/10324/52532
10.3390/md16110421
421
11
Marine Drugs
16
1660-3397
eng
https://www.mdpi.com/1660-3397/16/11/421
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2018 The Authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/52532/4/Synthesis-%20of-polysubstituted.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/52532
oai:uvadoc.uva.es:10324/548182023-03-02T08:33:29Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Addition of amines to molasses and lees as corrosion inhibitors in sustainable de-icing materials
Cherubin, Alberto
Guerra Navarro, Francisco Javier
Barrado Esteban, Enrique
García-Serrada, Carlos
Pulido Pelaz, Francisco José
Molasses
Melaza
Triethanolamine
Trietanolamina
Producción Científica
The waste formed during sugar- and wine-making activities has attracted our attention given its ability to inhibit corrosion in the presence of brine in a de-icing formulation. Herein the addition of amines to de-sugared beet molasses and winery lees is found to improve their anti-corrosive properties. Thus, weight-loss experiments clearly show that the addition of a small amount of amines to molasses or lees results in marked corrosion inhibition on carbon and galvanized steel. Subsequent electrochemical experiments and microscopy studies supported this finding. In addition, microscopy images indicated that triethanolamine was the best candidate amongst the amines tested for use in the final de-icing formulation. Ice-melting experiments demonstrated that the presence of molasses/lees together with triethanolamine does not alter the properties of the de-icing agent. When corrosion on galvanized and carbon steel probes was measured under environmental conditions, a decrease of 88% for galvanized steel and 65% for carbon steel was achieved due to the inhibiting action of the molasses/triethanolamine mixture. These results suggest that the addition of molasses/lees and triethanolamine to brine-based de-icing agents is recommended.
Junta de Castilla y Leon - Fondo Europeo de Desarrollo Regional (project 04/8/VA0013)
2022-09-01T11:43:49Z
2022-09-01T11:43:49Z
2022
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Sustainable Chemistry and Pharmacy, 2022, vol. 29, 100789
2352-5541
https://uvadoc.uva.es/handle/10324/54818
10.1016/j.scp.2022.100789
eng
https://www.sciencedirect.com/science/article/pii/S2352554122001930
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
© 2022 The Authors
application/pdf
Elsevier
https://uvadoc.uva.es/bitstream/10324/54818/4/Addition-amines-molasses-lees.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/54818
oai:uvadoc.uva.es:10324/559832022-10-18T19:01:46Zcom_10324_1170com_10324_931com_10324_894com_10324_1187col_10324_1367col_10324_1408
Descriptive statistical analysis of vegetable oil combustion in a commercial burner to establish optimal operating conditions
San José Alonso, Julio Francisco
Arroyo Gómez, Yolanda
Sanz Tejedor, María Ascensión
Rapeseed oil
Aceite de colza
Sunflower oil
Aceite de girasol
Biofuels
Biocombustibles
Combustion
Combustión
Producción Científica
This article studies the combustion of refined sunflower, virgin sunflower and virgin rapeseed oils in a low-pressure auxiliary air fluid pulverization burner in order to establish the optimal operating conditions. The influence of varying the type of vegetable oil, fuel flow rate and secondary airflow rate in the combustion process was analyzed. These three factors are independent in the combustion process, which means having to carry out numerous assays, combining the various factors with one another. Given the amount of variables to be optimized and the existence of three factors, a statistical approach is adopted to help interpret the results obtained and to evaluate how each factor influences the combustion results. Optimal combustion is determined based on three criteria, minimum pollutant emissions (CO, NOx and CxHy), maximum combustion performance, and minimum excess air. The result of this study showed that airflow was the principal factor affecting emissions, whereas for combustion performance, both factors (airflow and fuel flow) were determinant. In general, admissible combustion performances were obtained, with CO and NOx emissions below permitted levels. The best combustion performance was achieved under conditions of maximum fuel flow and minimum airflow rates.
Junta de Castilla y Leon - Fondo Europeo de Desarrollo Regional (project VA272P18)
2022-10-18T08:32:15Z
2022-10-18T08:32:15Z
2019
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Energies, 2019, vol. 12, n. 12, 2372
1996-1073
https://uvadoc.uva.es/handle/10324/55983
10.3390/en12122372
eng
https://www.mdpi.com/1996-1073/12/12/2372
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2019 The Authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/55983/4/Descriptive-statistical-analysis-vegetable-oil.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/55983
oai:uvadoc.uva.es:10324/560042023-10-06T08:04:02Zcom_10324_28542com_10324_952com_10324_894com_10324_1187com_10324_931col_10324_28543col_10324_1408
Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
Gil Ordóñez, Marta
Aubry, Camille
Niño, Cristopher
Maestro Fernández, Alicia
Andrés García, José María
Organocatalysis
Organocatálisis
Ketimines
Cetiminas
Pyrazolone
Pirazolona
Producción Científica
A series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in enantioselective Mannich reactions with different 1,3-dicarbonyl compounds. This method provides a direct pathway to access the 4-amino-5-pyrazolone derivatives bearing a quaternary substituted stereocenter and containing two privileged structure motifs, the β-diketone and pyrazolinone substructures. The adducts were obtained in excellent yields (up to 90%) and enantioselectivities (up to 94:6 er) by employing a very low loading of 2 mol% of a quinine-derived bifunctional squaramide as an organocatalyst for a wide range of substrates. In addition, the utility of the obtained products was demonstrated through one step transformations to enantioenriched diheterocyclic systems (4-pyrazolyl-pyrazolone and 4-isoxazolyl-pyrazolone), potentially promising candidates for drug discovery.
2022-10-19T08:46:32Z
2022-10-19T08:46:32Z
2022
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Molecules, 2022, vol. 27, n. 20, 6983
1420-3049
https://uvadoc.uva.es/handle/10324/56004
10.3390/molecules27206983
eng
https://www.mdpi.com/1420-3049/27/20/6983
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2022 The Authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/56004/4/Squaramide-catalyzed-asymmetric-Mannich-reaction.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/56004
oai:uvadoc.uva.es:10324/588442023-03-07T20:00:36Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Organocatalytic asymmetric synthesis of oxazolidino spiropyrazolinones via N,O-acetalization/aza Michael addition domino reaction between N-Boc pyrazolinone ketimines and γ-hydroxyenones
Gil Ordóñez, Marta
Martín Maroto, Laura
Maestro Fernández, Alicia
Andrés García, José María
Organocatalytic asymmetric synthesis
Síntesis organocatalítica
23 Química
Producción Científica
A squaramide-catalyzed asymmetric N,O-acetalization/aza Michael addition domino reaction between N-Boc ketimines derived from pyrazolin-5-ones and γ-hydroxyenones has been developed for the construction of pyrazolinone embedded spirooxazolidines. A hydroquinine derived bifunctional squaramide catalyst was found to be the most effective for this cascade spiroannulation. This new protocol allows the generation of two stereocenters and the desired products are obtained in good yields with moderate to good diastereoselectivities (up to 3.3 : 1 dr) and high enantioselectivities (up to >99% ee) from a range of substituted N-Boc pyrazolinone ketimines and γ-hydroxyenones. The developed protocol is amenable for a scale-up reaction.
Junta de Castilla y Leon (program EDU/556/2019)
2023-03-07T08:45:46Z
2023-03-07T08:45:46Z
2023
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
Organic and Biomolecular Chemistry, 2023
1477-0520
https://uvadoc.uva.es/handle/10324/58844
10.1039/D2OB02290G
Organic & Biomolecular Chemistry
1477-0539
eng
https://pubs.rsc.org/en/content/articlelanding/2023/ob/d2ob02290g
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
© The Royal Society of Chemistry 2023
application/pdf
Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/58844/4/Organocatalytic-Asymmetric-Synthesis.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by-nc-nd/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/58844
oai:uvadoc.uva.es:10324/592132023-04-19T19:00:33Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
Díez Poza, Carlos
Barbero Pérez, María Asunción
Química orgánica
Organic chemistry
Tetrahydropyrans
Tetrahydrofurans
Cyclization
Epoxysilyl alcohols
Side reaction
Tandem process
Producción Científica
The regioselective ring opening of epoxy alcohols is an effective method for the synthesis of different types of oxacycles. The 5-exo opening being preferred vs. the 6-endo mode, according to Baldwin rules, the use of silyl-substituted oxiranes has been reported as a possible method to favor the 6-endo cyclization. However, there is a need for a detailed study on the different factors (structural factors, catalyst nature or conditions) that influence this process. In this paper, the acid-catalyzed cyclization of epoxysilyl alcohols was studied, focusing on the effect of substituents and reaction conditions on the outcome of the process. Two types of heterocycles (tetrahydrofurans or tetrahydropyrans) were selectively obtained depending on the structure of the initial epoxysilyl alcohol. Interestingly, cyclization of hindered epoxysilyl alcohols mainly proceeds through an unexpected side reaction, which implies a previous isomerization to an aldehyde. A mechanistic proposal for the formation of the different products is presented.
Junta de Castilla y León - (Project VA294-P18)
Fondo Social Europeo y Junta de Castilla y León - (Grant Q4718001C)
jun
2023-04-19T11:09:10Z
2023-04-19T11:09:10Z
2021
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Molecules, 2021, Vol. 26, Nº. 23, 7386
1420-3049
https://uvadoc.uva.es/handle/10324/59213
10.3390/molecules26237386
7386
23
Molecules
26
1420-3049
eng
https://www.mdpi.com/1420-3049/26/23/7386
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2021 The authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/59213/5/Influence-of-the-Substituents-on-the-Opening-of-Silylepoxy-Alcohols.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/59213
oai:uvadoc.uva.es:10324/595302023-05-08T19:00:43Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Theoretical three-dimensional zinc complexes with glutathione, amino acids and flavonoids
Pérez de la Lastra, José Manuel
Andrés Juan, Celia
Plou Gasca, Francisco José
Pérez Lebeña, Eduardo
Zinc
Polyphenols
Glutathione - Therapeutic use
Natural products
Aminoácidos
Flavonoids
Dietary supplements
Natural products
Producción Científica
Zinc plays an important role in the regulation of many cellular functions; it is a signaling molecule involved in the transduction of several cascades in response to intra and extracellular stimuli. Labile zinc is a small fraction of total intracellular zinc, that is loosely bound to proteins and is easily interchangeable. At the cellular level, several molecules can bind labile zinc and promote its passage across lipophilic membranes. Such molecules are known as ionophores. Several of these compounds are known in the scientific literature, but most of them can be harmful to human health and are therefore not allowed for medical use. We here performed a theoretical three-dimensional study of known zinc ionophores, together with a computational energetic study and propose that some dietary flavonoids, glutathione and amino acids could form zinc complexes and facilitate the transport of zinc, with the possible biological implications and potential health benefits of these natural compounds. The study is based on obtaining a molecular conformational structure of the zinc complexes with the lowest possible energy content. The discovery of novel substances that act as zinc ionophores is an attractive research topic that offers exciting opportunities in medicinal chemistry. We propose that these novel complexes could be promising candidates for drug design to provide new solutions for conditions and diseases related to zinc deficiency or impairment derived from the dysregulation of this important metal.
Junta de Castilla y León y Fondo Europeo de Desarrollo Regional (FEDER) - (Projects VA115P17 and VA149G18)
Fondo Europeo de Desarrollo Regional (FEDER) y Agencia Canaria de Investigación, Innovación y Sociedad de la Información (ACIISI) del Gobierno de Canarias - (Project ProID2020010134)
CajaCanarias (project 2019SP43)
Ministerio de Economía, Industria y Competitividad - (Grant PID2019-105838RB-C31)
2023-05-08T10:47:17Z
2023-05-08T10:47:17Z
2021
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Stresses, 2021, Vol. 1, Nº. 3, págs 123-141
2673-7140
https://uvadoc.uva.es/handle/10324/59530
10.3390/stresses1030011
123
3
141
Stresses
1
2673-7140
eng
https://www.mdpi.com/2673-7140/1/3/11
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2021 The authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/59530/4/Theoretical-Three-Dimensional-Zinc-Complexes.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/59530
oai:uvadoc.uva.es:10324/596822023-06-05T19:01:13Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Access to Spiropyrazolone-butenolides through NHC-Catalyzed [3 + 2]-Asymmetric Annulation of 3-Bromoenals and 1H-Pyrazol-4,5-diones
Gil Ordóñez, Marta
Maestro Fernández, Alicia
Andrés García, José María
Química
Química orgánica
Organocatalysis
Spirobutenolides
Enantioselectivities
Organocatálisis
Espirobutenólidos
Enantioselectividades
23 Química
Producción Científica
The stereoselective synthesis of spirocyclic pyrazo-
lin-5-ones by N-heterocyclic carbene (NHC) organocatalysis has
been less studied so far. For this reason and considering the interest
of this class of compounds, here, we present the NHC-catalyzed [3
+ 2]-asymmetric annulation of β-bromoenals and 1H-pyrazol-4,5-
diones that achieves to produce chiral spiropyrazolone-butenolides.
The synthesis is general for aryl and heteroaryl β-bromo-α,β-
unsaturated aldehydes and 1,3-disubstituted pyrazolones. The
spirobutenolides have been obtained in good yields (up to 88%)
and enantioselectivities (up to 97:3 er). This constitutes the first
described example using pyrazoldiones as the starting materials for
this class of spiro compounds.
Junta de Castilla y León predoctoral fellowship (EDU/556/2019)
2023-05-23T07:16:35Z
2023-05-23T07:16:35Z
2023
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
The Journal of Organic Chemistry, 2023, vol. 88, n. 11, pp. 6890–6900
0022-3263
https://uvadoc.uva.es/handle/10324/59682
10.1021/acs.joc.3c00188
The Journal of Organic Chemistry
1520-6904
eng
https://pubs.acs.org/doi/10.1021/acs.joc.3c00188
Atribución 4.0 Internacional
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2023 The Authors
application/pdf
American Chemical Society
https://uvadoc.uva.es/bitstream/10324/59682/5/Access-to-Spiropyrazolone-butenolides.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/59682
oai:uvadoc.uva.es:10324/597042023-06-05T19:00:59Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Changing the reaction pathway of Silyl-Prins cyclization by switching the lewis acid: Application to the synthesis of an antinociceptive compound
Díez Poza, Carlos
Fernández Peña, Laura
González Andrés, Paula
Barbero Pérez, María Asunción
Química
Química orgánica
Catalysis
Synthesis of tetrahydropyrans
Lewis acid
Antinociceptive
Síntesis de tetrahidropiranos
Ácido de Lewis
Antinociceptivo
2306 Química Orgánica
Producción Científica
Developing new procedures for the synthesis of tetrahydropyrans in a very stereoselective manner is of great importance for the synthesis of THP-containing natural products. Here, we report an interesting protocol for the synthesis of polysubstituted halogenated tetrahydropyrans by silyl-Prins cyclization of vinylsilyl alcohols, in which the nature of the Lewis acid determines the outcome of the process. The methodology has been applied to the synthesis of a known antinociceptive.
Junta de Castilla y León (VA294P18)
2023-05-29T08:37:43Z
2023-05-29T08:37:43Z
2023
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
The Journal of Organic Chemistry, 2023, vol. 88, n. 11, pp. 6776–6783
0022-3263
https://uvadoc.uva.es/handle/10324/59704
10.1021/acs.joc.3c00050
The Journal of Organic Chemistry
1520-6904
eng
https://pubs.acs.org/doi/full/10.1021/acs.joc.3c00050
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2023 The Authors
application/pdf
American Chemical Society
https://uvadoc.uva.es/bitstream/10324/59704/5/Changing-the-Reaction-Pathway.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/59704
oai:uvadoc.uva.es:10324/599222023-06-21T19:00:36Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Marine heterocyclic compounds that modulate intracellular calcium signals: Chemistry and synthesis approaches
González Andrés, Paula
Fernández Peña, Laura
Díez Poza, Carlos
Villalobos Jorge, Carlos
Núñez Llorente, Lucía
Barbero Pérez, María Asunción
Organic chemistry
Drugs
Drogas
Heterocyclic compounds
Compuestos heterocíclicos
Pharmacology/Toxicology
Calcio en el organismo
Calcio, Conductos de
Organic compounds - Synthesis
Compuestos orgánicos - Síntesis
Clinical chemistry
Drug development
Medicamentos - Investigación
Marine drugs
Drogas marinas
3209 Farmacología
3214 Toxicología
Producción Científica
Intracellular Ca2+ plays a pivotal role in the control of a large series of cell functions in all types of cells, from neurotransmitter release and muscle contraction to gene expression, cell proliferation and cell death. Ca2+ is transported through specific channels and transporters in the plasma membrane and subcellular organelles such as the endoplasmic reticulum and mitochondria. Therefore, dysregulation of intracellular Ca2+ homeostasis may lead to cell dysfunction and disease. Accordingly, chemical compounds from natural origin and/or synthesis targeting directly or indirectly these channels and proteins may be of interest for the treatment of cell dysfunction and disease. In this review, we show an overview of a group of marine drugs that, from the structural point of view, contain one or various heterocyclic units in their core structure, and from the biological side, they have a direct influence on the transport of calcium in the cell. The marine compounds covered in this review are divided into three groups, which correspond with their direct biological activity, such as compounds with a direct influence in the calcium channel, compounds with a direct effect on the cytoskeleton and drugs with an effect on cancer cell proliferation. For each target, we describe its bioactive properties and synthetic approaches. The wide variety of chemical structures compiled in this review and their significant medical properties may attract the attention of many different researchers.
Ministerio de Ciencia e Innovación - (grant RTI2018-099298-B-100)
Junta de Castilla y León - (grant VA294-P18)
2023-06-21T11:07:01Z
2023-06-21T11:07:01Z
2021
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Marine Drugs, 2021, Vol. 19, Nº. 2, 78
1660-3397
https://uvadoc.uva.es/handle/10324/59922
10.3390/md19020078
78
2
Marine Drugs
19
1660-3397
eng
https://www.mdpi.com/1660-3397/19/2/78
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2021 The authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/59922/4/Marine-Heterocyclic-Compounds.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/59922
oai:uvadoc.uva.es:10324/607002023-08-18T19:00:59Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Recent advances in biologically active coumarins from marine sources: Synthesis and evaluation
Fernández Peña, Laura
Matos, Maria João
López Hernández, Enol
Cumarina
Natural products
Productos naturales
Organic chemistry
Biochemistry
Compuestos heterocíclicos
Marine ecology
Ecología marina
Heterocyclic compounds
Drugs
Medicamentos
Pharmacology
2306 Química Orgánica
3209 Farmacología
Producción Científica
Coumarin and its derivatives have significantly attracted the attention of medicinal chemists and chemical biologists due to their huge range of biological, and in particular, pharmacological properties. Interesting families of coumarins have been found from marine sources, which has accelerated the drug discovery process by inspiring innovation or even by the identification of analogues with remarkable biological properties. The purpose of this review is to showcase the most interesting marine-derived coumarins from a medicinal chemistry point of view, as well as the novel and useful synthetic routes described to date to achieve these chemical structures. The references that compose this overview were collected from PubMed, Mendeley and SciFinder.
Junta de Castilla y León - (grant VA294-P18)
Ministerio de Ciencia e Innovación - (PID2020-116076RJI00/AEI/10.13039/501100011033)
2023-08-18T08:28:16Z
2023-08-18T08:28:16Z
2023
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Marine Drugs, 2023, Vol. 21, Nº. 1, 37
1660-3397
https://uvadoc.uva.es/handle/10324/60700
10.3390/md21010037
37
1
Marine Drugs
21
1660-3397
eng
https://www.mdpi.com/1660-3397/21/1/37
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2022 The Authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/60700/4/Recent-Advances-in-Biologically-Active-Coumarins-from-Marine-Sources.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/60700
oai:uvadoc.uva.es:10324/615962023-09-15T19:00:32Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
The tetrahydrofuran motif in marine lipids and terpenes
González Andrés, Paula
Fernández Peña, Laura
Díez Poza, Carlos
Barbero Pérez, María Asunción
Marine natural products
Natural products
Productos naturales
Heterocyclic compounds
Tetrahydrofuran
Organic compounds - Synthesis
Compuestos orgánicos - Síntesis
Biological activity
Terpenes
Terpenos - Biosíntesis
Lipids
Lípidos
Fatty acid
Organic chemistry
Drug development
Medicamentos - Investigación
Farmacology - Research
2306 Química Orgánica
2306.10 Compuestos Heterocíclicos
3209 Farmacología
Producción Científica
Heterocycles are particularly common moieties within marine natural products. Specifically, tetrahydrofuranyl rings are present in a variety of compounds which present complex structures and interesting biological activities. Focusing on terpenoids, a high number of tetrahydrofuran-containing metabolites have been isolated during the last decades. They show promising biological activities, making them potential leads for novel antibiotics, antikinetoplastid drugs, amoebicidal substances, or anticancer drugs. Thus, they have attracted the attention of the synthetics community and numerous approaches to their total syntheses have appeared. Here, we offer the reader an overview of marine-derived terpenoids and related compounds, their isolation, structure determination, and a special focus on their total syntheses and biological profiles.
Junta de Castilla y León - (grant VA294-P18)
2023-09-15T11:47:59Z
2023-09-15T11:47:59Z
2022
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Marine Drugs, 2022, Vol. 20, Nº. 10, 642
1660-3397
https://uvadoc.uva.es/handle/10324/61596
10.3390/md20100642
642
10
Marine Drugs
20
1660-3397
eng
https://www.mdpi.com/1660-3397/20/10/642
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2022 The Authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/61596/4/The-Tetrahydrofuran-Motif-in-Marine-Lipids-and-Terpenes.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/61596
oai:uvadoc.uva.es:10324/620592023-10-18T19:01:21Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
The tetrahydrofuran motif in polyketide marine drugs
Fernández Peña, Laura
Díez Poza, Carlos
González Andrés, Paula
Barbero Pérez, María Asunción
Marine natural products
Productos naturales
Heterocyclic compounds
Compuestos heterocíclicos
Tetrahydrofuran
Organic compounds - Synthesis
Compuestos orgánicos - Síntesis
Biological activity
Marine pharmacology
Natural products - Therapeutic use
Drugs
Medicamentos
2306 Química Orgánica
3209 Farmacología
Producción Científica
Oxygen heterocycles are units that are abundant in a great number of marine natural products. Among them, marine polyketides containing tetrahydrofuran rings have attracted great attention within the scientific community due to their challenging structures and promising biological activities. An overview of the most important marine tetrahydrofuran polyketides, with a focused discussion on their isolation, structure determination, approaches to their total synthesis, and biological studies is provided.
Junta de Castilla y León - (grant VA294-P18)
2023-10-18T12:45:13Z
2023-10-18T12:45:13Z
2022
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Marine Drugs, 2022, Vol. 20, Nº. 2, 120
1660-3397
https://uvadoc.uva.es/handle/10324/62059
10.3390/md20020120
120
2
Marine Drugs
20
1660-3397
eng
https://www.mdpi.com/1660-3397/20/2/120
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2022 The Authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/62059/4/The-Tetrahydrofuran-Motif-in-Polyketide-Marine-Drugs.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/62059
oai:uvadoc.uva.es:10324/630622023-11-17T20:01:06Zcom_10324_28542com_10324_952com_10324_894com_10324_1187com_10324_931col_10324_28543col_10324_1408
Dimethylzinc-mediated enantioselective addition of terminal alkynes to 1,2-diketones using perhydro-1,3-benzoxazines as ligands
Prieto, Elena
Infante, Rebeca
Nieto Román, Francisco Javier
Andrés Juan, Celia
Catálisis enantioselectiva, compuestos organozíncicos, 1,2-dicetonas, alfa-alquinil-alfa-hidroxicetonas
2306.99 Química Orgánica-Síntesis enantioselectiva
Producción Científica
A conformationally restricted perhydro-1,3-benzoxazine derived from (−)-8-aminomenthol behaves as a
good chiral ligand in the dimethylzinc-mediated enantioselective monoaddition of aromatic and aliphatic
terminal alkynes to 1,2-diketones. The corresponding α-hydroxyketones were obtained in good yields
with high enantioselectivities starting from both aromatic and aliphatic 1,2-diketones. The alkynylation of
unsymmetrical 1,2-diketones with electronically different substituents also proceeds with high regio- and
enantioselectivity. This reaction provides a practical method to synthesize ketones bearing a chiral tertiary
propargylic alcohol.
Junta de Castilla y León, proyectos FEDER-VA115P17 y VA149G18
2023-11-17T10:26:11Z
2023-11-17T10:26:11Z
2021
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
Organic and Biomolecular. Chemistry, 2021, vol. 19, n 17, p 3859-3867
1477-0520
https://uvadoc.uva.es/handle/10324/63062
10.1039/d1ob00249j
3859
17
3867
Organic & Biomolecular Chemistry
19
1477-0539
eng
https://pubs.rsc.org/en/content/articlelanding/2021/ob/d1ob00249j
info:eu-repo/semantics/restrictedAccess
The Royal Society of Chemistry
application/pdf
The Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/63062/3/OBC%20%20accepted%20manuscript_2021.pdf.jpg
Hispana
TEXT
http://rightsstatements.org/vocab/CNE/1.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/63062
oai:uvadoc.uva.es:10324/630632023-11-17T20:01:08Zcom_10324_28542com_10324_952com_10324_894com_10324_1187com_10324_931col_10324_28543col_10324_1408
Enantioselective synthesis of 3-hydroxy- and 3-amino-3-alkynyl-2-oxindoles by the dimethylzinc-mediated addition of terminal alkynes to isatins and isatin-derived ketimines
Prieto, Elena
Martín, Jorge D.
Nieto Román, Francisco Javier
Andrés Juan, Celia
Catálisis enantioselectiva, compuestos organozíncicos, alquinilación, isatinas e iminas derivadas de isatinas
2306.99 Química Orgánica-Síntesis enatioselectiva
Producción Científica
A common protocol for enantioselective alkynylation of isatins and isatin-derived ketimines using terminal
alkynes and Me2Zn in the presence of a catalytic amount of a chiral perhydro-1,3-benzoxazine with moderate to excellent enantioselectivity under mild reaction conditions is described. The additions to ketimines present a novel approach to chiral amines being derivatives of oxindoles. The reaction is broad in scope with respect to aryl- and alkyl-substituted terminal alkynes and isatin derivatives. In isatins, the alkynylation occurs at the Si face of the carbonyl group, whereas in the ketimine derivatives it occurs at the Re face of the imine.
Junta de Castilla y León, proyectos FEDER-VA115P17 y VA149G18
2023-11-17T10:38:02Z
2023-11-17T10:38:02Z
2023
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
Organic and Biomolecular. Chemistry, 2023, vol.21, n 34, p 6940-69-48
1477-0520
https://uvadoc.uva.es/handle/10324/63063
10.1039/d3ob01023f
6940
34
6948
Organic & Biomolecular Chemistry
21
1477-0539
spa
https://pubs.rsc.org/en/content/articlelanding/2023/ob/d3ob01023f
info:eu-repo/semantics/openAccess
The Royal Society of Chemistry
application/pdf
The Royal Society of Chemistry
https://uvadoc.uva.es/bitstream/10324/63063/3/OBC%20%20accepted%20manuscript_2023.pdf.jpg
Hispana
TEXT
http://rightsstatements.org/vocab/CNE/1.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/63063
oai:uvadoc.uva.es:10324/638002024-01-15T13:07:35Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Enantioselective amination of 4-substituted pyrazolones catalyzed by oxindole-containing thioureas and by a recyclable linear-polymer-supported analogue in a continuous flow process
Sánchez Molpeceres, Rodrigo
Martín Maroto, Laura
Esteban Hernández, Isabel Noelia
Miguel García, Jesús Ángel
Maestro Fernández, Alicia
Andrés García, José María
Química orgánica
Polimeros y polimerización
Aromatic compounds
Catalysts
Mixtures
Compuestos aromáticos
Catalizadores
Mezclas
2306 Química Orgánica
Producción Científica
A highly efficient organocatalytic amination of 4-substituted pyrazolones with azodicarboxylates mediated by a novel quinine-derived thiourea with a 3,3-diaryl-oxindole scaffold is reported. This synthetic method furnished 4-amino-5-pyrazolones in high yields and with excellent enantioselectivities (up to 97:3 er) at room temperature in short reaction times. Moreover, a linear-polymer-supported bifunctional thiourea, synthesized by reacting a bifunctional aromatic monomer (biphenyl) with isatin in superacidic media and further derivatization, was proven to be also an efficient heterogeneous organocatalyst for this α-amination reaction. The practical value of this process was demonstrated by the use of the immobilized catalyst in recycling experiments, maintaining the activity without additional reactivation, and in flow processes, allowing the synthesis of 4-amino-pyrazolone derivatives in a gram scale with high yield and enantioselectivity.
Agencia Estatal de Investigación- FEDER-UE (PID2020-118547GB-I00)
Junta de Castilla y León (VA224P20)
2023-12-22T09:43:21Z
2023-12-22T09:43:21Z
2023
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
The Journal Of Organic Chemistry, 2024, vol. 89, n.1, pp. 330-344
0022-3263
https://uvadoc.uva.es/handle/10324/63800
10.1021/acs.joc.3c02069
The Journal of Organic Chemistry
1520-6904
eng
https://pubs.acs.org/doi/10.1021/acs.joc.3c02069
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2023 The Authors
application/pdf
American Chemical Society
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Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/63800
oai:uvadoc.uva.es:10324/638112023-12-22T20:00:55Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
Fernández Peña, Laura
López Hernández, Enol
Sánchez González, Ángel
Barbero Pérez, María Asunción
Heterocyclic compounds
Compuestos heterocíclicos
Analytical chemistry
Prins cyclization
Oxacycles
2301 Química Analítica
Producción Científica
A convenient regioselective synthesis of allyl- and vinylsilyl alcohols, from a common precursor, was described, by selecting the appropriate reaction conditions. Allyl- and vinylsilyl alcohols were tested in silyl-Prins cyclizations for the preparation of disubstituted oxygenated heterocycles in a one-pot sequential reaction. The methodology was sensitive to the structure of the starting alkenylsilyl alcohol and reaction conditions, with competitive pathways observed (particularly for allylsilyl alcohols), such as Peterson elimination and oxonia-Cope reactions. However, the use of vinylsilyl alcohols allowed the preparation of differently disubstituted cis-2,6-dihydropyrans in moderate to good yields. Computational studies support the proposed mechanism.
Junta de Castilla y León - (grant VA294-P18)
Ministerio de Ciencia e Innovación - (PID2020-116076RJI00/AEI/10.13039/501100011033)
2023-12-22T12:17:07Z
2023-12-22T12:17:07Z
2023
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Molecules, 2023, Vol. 28, Nº. 7, 3080
1420-3049
https://uvadoc.uva.es/handle/10324/63811
10.3390/molecules28073080
3080
7
Molecules
28
1420-3049
eng
https://www.mdpi.com/1420-3049/28/7/3080
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2023 The authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/63811/4/Diastereoselective-Synthesis.pdf.jpg
Hispana
TEXT
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UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/63811
oai:uvadoc.uva.es:10324/665462024-03-06T20:00:49Zcom_10324_1187com_10324_931com_10324_894col_10324_1408
Continuous flow chemistry: A novel technology for the synthesis of marine drugs
Fernández Peña, Laura
González Andrés, Paula
Parte, Lucía G.
Escribano, Raúl
Guerra, Javier
Barbero Pérez, María Asunción
López Hernández, Enol
Flow chemistry
Drug development
Pharmaceutical chemistry
Photochemistry
Drugs
Marine pharmacology
Pharmacology
Drug development
Medicamentos - Investigación
Pharmaceutical technology
Medicinal chemistry
Innovaciones Tecnológicas
2306 Química Orgánica
2210.22 Fotoquímica
3209 Farmacología
3209.01 Análisis de Medicamentos
Producción Científica
In this perspective, we showcase the benefits of continuous flow chemistry and photochemistry and how these valuable tools have contributed to the synthesis of organic scaffolds from the marine environment. These technologies have not only facilitated previously described synthetic pathways, but also opened new opportunities in the preparation of novel organic molecules with remarkable pharmacological properties which can be used in drug discovery programs.
Ministerio de Ciencia e Innovación - (grants TED2021-131705B-C21 and PID2021-125909OB-I00)
2024-03-06T13:49:38Z
2024-03-06T13:49:38Z
2023
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Marine Drugs, 2023, Vol. 21, Nº. 7, 402
1660-3397
https://uvadoc.uva.es/handle/10324/66546
10.3390/md21070402
402
7
Marine Drugs
21
1660-3397
eng
https://www.mdpi.com/1660-3397/21/7/402
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2023 The authors
application/pdf
MDPI
https://uvadoc.uva.es/bitstream/10324/66546/4/Continuous-Flow-Chemistry.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
UVaDOC. Repositorio Documental de la Universidad de Valladolid
https://uvadoc.uva.es/handle/10324/66546