One-pot synthesis of epoxides from benzyl alcohols and aldehydes

Abstract

A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.

Keywords

• Corey–Chaykovsky
• epoxide
• heterocycle
• one-pot
• ylide