Synthesis 2013; 45(19): 2669-2678
DOI: 10.1055/s-0033-1338922
special topic
© Georg Thieme Verlag Stuttgart · New York

A Simple Synthesis of Polysubstituted Pyrrolidines by an Organocatalytic Three-Component Approach Featuring a One-Pot Condensation and [3+2]-Cycloaddition Reaction in Aqueous Medium

Silvia Reboredo
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain   Fax: +34(94)6012748   Email: joseluis.vicario@ehu.es
,
Jose L. Vicario*
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain   Fax: +34(94)6012748   Email: joseluis.vicario@ehu.es
,
Luisa Carrillo
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain   Fax: +34(94)6012748   Email: joseluis.vicario@ehu.es
,
Efraím Reyes
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain   Fax: +34(94)6012748   Email: joseluis.vicario@ehu.es
,
Uxue Uria
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain   Fax: +34(94)6012748   Email: joseluis.vicario@ehu.es
› Author Affiliations
Further Information

Publication History

Received: 14 February 2013

Accepted: 15 April 2013

Publication Date:
11 June 2013 (online)

Abstract

A simple one-pot procedure was developed for [3+2]-cycloaddition reactions of α,β-unsaturated aldehydes, diethyl aminomalonate, and aromatic aldehydes in the presence of diphenyl[(2S)-pyrrolidin-2-yl]methanol as catalyst. This reaction converts simple, commercially available, starting materials into densely functionalized polysubstituted pyrrolidines under mild conditions and in a fully stereoselective fashion. Moreover, the use of brine as the reaction medium has remarkable beneficial effects in preventing the formation of self-condensation byproducts, cutting the reaction time, and reducing the production of wastes.

Supporting Information

 
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