Asymmetric Epoxidation in Stereoselective Synthesis

Asymmetric epoxidation of olefins has been proven to be one of the most important methods to generate chiral epoxides, which are highly useful intermediates in the stereoselective synthesis of biologically interesting compounds. In this chapter, several powerful and practical asymmetric epoxidation methods and their utilities for the stereoselective synthesis of drug substances and natural products are described. The representative asymmetric epoxidation methods that are described in the chapter include directed epoxidations, metal oxo-catalyzed epoxidations, dioxirane-catalyzed epoxidations, nucleophilic epoxidations, and asymmetric phase-transfer–catalyzed epoxidations. Keywords: asymmetric epoxidation; stereoselective; C–O bond formation; synthesis; directed epoxidation; metal oxo-catalyzed epoxidation; manganese; chromium; Sharpless epoxidation; Jacobsen epoxidation; dioxirane-catalyzed epoxidation; nucleophilic epoxidation; phase-transfer; Mn-salen catalyst; Cr-salen catalyst; Jacobsen-Katsuki epoxidation; oxone