2026-05-14T03:50:58Zhttps://uvadoc.uva.es/oai/request

oai:uvadoc.uva.es:10324/560042023-10-06T08:04:02Zcom_10324_28542com_10324_952com_10324_894com_10324_1187com_10324_931col_10324_28543col_10324_1408

Gil Ordóñez, Marta 7ce601cf40cfdd85 600 Aubry, Camille b90e6d8a-43bf-4a54-97db-f457f9c5b846 600 Niño, Cristopher ce2fecc9-ef44-4fc3-aa4a-aebaaad4b662 600 Maestro Fernández, Alicia 384c61511fee9897 600 0000-0003-1941-6981 Andrés García, José María bf59b6ca8a595a1b 600 0000-0002-0595-3789 2022-10-19T08:46:32Z 2022-10-19T08:46:32Z 2022 Molecules, 2022, vol. 27, n. 20, 6983 1420-3049 https://uvadoc.uva.es/handle/10324/56004 10.3390/molecules27206983 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. application/pdf eng MDPI info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/4.0/ © 2022 The Authors Atribución 4.0 Internacional Organocatalysis Organocatálisis Ketimines Cetiminas Pyrazolone Pirazolona 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 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion https://www.mdpi.com/1420-3049/27/20/6983 SI THUMBNAIL Squaramide-catalyzed-asymmetric-Mannich-reaction.pdf.jpg Squaramide-catalyzed-asymmetric-Mannich-reaction.pdf.jpg IM Thumbnail image/jpeg 4710 https://uvadoc.uva.es/bitstream/10324/56004/4/Squaramide-catalyzed-asymmetric-Mannich-reaction.pdf.jpg f9499d4201d736772a1554666abe8bb7 MD5 4 LICENSE license.txt license.txt text/plain 3929 https://uvadoc.uva.es/bitstream/10324/56004/3/license.txt 289d98c1665ee0d20312360f0e8643c8 MD5 3 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 921 https://uvadoc.uva.es/bitstream/10324/56004/2/license_rdf 9eecc1514e7247cad41e4db756248760 MD5 2 ORIGINAL Squaramide-catalyzed-asymmetric-Mannich-reaction.pdf Squaramide-catalyzed-asymmetric-Mannich-reaction.pdf application/pdf 920598 https://uvadoc.uva.es/bitstream/10324/56004/1/Squaramide-catalyzed-asymmetric-Mannich-reaction.pdf b473e3d53123a2f3423777cdf0520ff6 MD5 1 10324/56004 oai:uvadoc.uva.es:10324/56004 2023-10-06 10:04:02.105 UVaDOC repositorio@uva.es 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