Stereoselective syntheses of substituted tert-butyl 3-allyl-4-hydroxypiperidine-1-carboxylate

Abstract

tert-Butyl 3-allyl-4-oxopiperidine-1-carboxylate and its derivatives substituted at the 3-position and in the allylic fragment reacted with L-selectride in anhydrous tetrahydrofuran to give tert-butyl (3R,4S)-3-allyl-4-hydroxypiperidine-1-carboxylates (cis isomers) in quantitative yield. The Mitsunobu reaction of the latter with formic or benzoic acid, followed by alkaline hydrolysis, afforded the corresponding trans (3R,4R) isomers.