2026-05-05T19:30:39Zhttps://uvadoc.uva.es/oai/requestoai:uvadoc.uva.es:10324/377192025-03-26T19:10:02Zcom_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
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
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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