6.21 C–X Bond Formation: Organocatalytic Enantioselective Halogenation of meso Epoxides

Abstract

The halogenation of meso epoxides is the reaction of a symmetrical epoxide, acting as an electrophile, with a halide, acting as a nucleophile, to produce a chiral halohydrin. In this chapter, we summarize the enantioselective halogenation of meso epoxides from a historical perspective and a mechanical scope. Ring-opening of meso epoxides with silicon tetrachloride and chiral Lewis bases has emerged as the effective strategy for the synthesis of chiral chlorohydrins.