Asymmetric Hetero Diels-Alder Reaction of N-Benzylimines Derived from R-Glyceraldehyde: A New Approach to Homochiral Piperidine Building Blocks and its Application to the Synthesis of (2 R)-4-Oxopipecolic Acid

Abstract

The N-Benzyl imine derived from 2,3-di- O-benzyl-D-glyceraldehyde reacts with Danishefsky's diene to afford the corresponding hetero Diels-Alder adduct with a high diastereoselectivity. This compound can be transformed to enantiomerically pure (2 R)-4-oxopipecolic acid. © 1997 Elsevier Science Ltd.