A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids.

Affiliation

Mittapalli RR(1), Coles SJ(2), Klooster WT(2), Dobbs AP(1).
Author information:
(1)School of Science, University of Greenwich, Chatham Maritime, Kent ME4 4TB, United Kingdom.
(2)UK National Crystallography Service, University of Southampton, University Road, Southampton SO17 1BJ, United Kingdom.

Abstract

The aza-Prins reaction is a widely employed and highly efficient method for the preparation of saturated nitrogen-containing heterocycles. Its major drawback has always been a lack of diastereoselectivity and the formation of racemic products. Herein, we address these problems and report, for the first time, the synthesis of both diastereomerically and enantiopure multiply substituted piperidines via the aza-Prins reaction. This method is widely applicable for natural product synthesis and is exemplified here by the synthesis of enantiopure pipecolic acid derivatives.