Asymmetric Epoxidation of Allylic Alcohols: The Sharpless Epoxidation

Abstract

The asymmetric epoxidation of allylic alcohols using t-butyl hydroperoxide in the presence of titanium tetraisopropoxide and a chiral dialkyl tartrate - the Sharpless epoxidation - is reviewed. Numerous examples taken from the syntheses of naturally occuring, enantiomerically pure compounds emphasise the synthetic versatility of this method. 1. Introduction 2. Asymmetric Epoxidation of Allylic Alcohols 3. Applications of the Sharpless Epoxidation 4. Further Developments of the Sharpless Epoxidation 5. Conclusions