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

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.