Mechanistic Studies on Racemization of chiral 2-arylthiazolidinones

摘要

Mechanistic studies on recemization of chiral 3-[(2S)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]propanoic acid is described.This racemization is triggered by deprotonatioin of phenolic hydroxyl group.We propose that the recemization proceeds via a novel mechanism involving ring opening-closure equilibrium of the thiazolidinone ring.