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

作者：Reboredo Silvia; Vicario Jose L^*; Carrillo Luisa; Reyes Efraim; Uria Uxue

来源：Synthesis, 2013, 45(19): 2669-2678.

DOI：10.1055/s-0033-1338922

• asymmetric catalysis
• asymmetric synthesis
• organocatalysis
• cycloadditions
• multicomponent reactions
• heterocycles

A simple one-pot procedure was developed for [3+2]-cycloaddition reactions of ,-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.

• 出版日期2013-10-1