Studies on the Catalytic Asymmetric Synthesis of Terminal Expoxides from Aldehydes

Abstract

Chiral non racemic terminal epoxides are among most the valuable building blocks available to an organic chemist. The Johnson-Corey-Chaykovksy epoxidation (JCC) of carbonyl compounds is a promising and complementary approach to the classic olefin oxidation methodologies. It represents an efficient and straightforward method for the synthesis of epoxides. However, the JCC enantioselective methylene transfer epoxidation benchmark literature protocols for the synthesis of optically active terminal epoxides are characterised by moderate product yields/enantioselectivity and the requirement for (super)stoichiometric catalyst loadings.