Cooperative Lewis acid-onium salt catalysis as tool for the desymmetrization of meso-epoxides

Chem Commun (Camb). 2017 Jan 17;53(6):1156-1159. doi: 10.1039/c6cc09774j.

Abstract

Epoxide desymmetrizations by bromide are very rare despite the large synthetic potential of chiral bromohydrins. Herein we present a new concept for epoxide desymmetrizations in which a bifunctional Lewis acid/ammonium salt catalyst allows for efficient enantioselective epoxide ring openings by Br-. With acetylbromide as a Br- source bromohydrin esters are formed.