Chiral Phosphoric Acid-Catalyzed Desymmetrization of <i>meso</i>-Aziridines with Functionalized Mercaptans

Abstract

Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso-aziridines, and a catalytic amount of VAPOL phosphoric acid to explore the substrate scope of this highly enantioselective reaction.