Organocatalytic enantioselective synthesis of epoxysulfones

Abstract

An epoxide is a three-member ring with one oxygen and two carbon atoms hence displaying a cyclic ether function. This ring approximates an equilateral triangle being highly reactive due to angle strain. For this reason, epoxides are synthesized more than other ethers and they are produced on a large scale for many applications. So, epoxides are considered one of the most important building blocks in organic chemistry. On the other hand, sulfones are excelent leaving groups because a sulfur atom is bonded to two oxygen atoms which are highly electronegative and have a high inductive effect, in addition sulfones can stabilize negative charges due to the size of sulfur atom. So, in conclusion epoxysulfones represent versatile building blocks in organic chemistry because the epoxide is highly reactive and the sulfone is an excelent leaving group. In this work the synthesis of epoxysulfones in an asymmetric fashion starting from aromatic ketones has been studied. Also the conversion of obtained epoxyxulfones into alcohols as precursors of NonSteroidal Anti-Inflamatory Drugs (NSAIDs) was studied.