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 (2R)-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 (2R)-4-oxopipecolic acid. © 1997 Elsevier Science Ltd.