Organocatalytic Properties of 3,4-Dihydroxyprolines

Abstract

The synthesis and organocatalytic properties of (2S,3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid are reported. Using the aldol condensation of cyclohexanone with p-nitrobenzaldehyde as a model, a yield of 86%, an enantiomeric excess of 99% and a diastereomeric excess of 25:1 were achieved.

Keywords

• organocatalysis
• prolines
• aldol condensation