Asymmetric Epoxidation of Homoallylic Alcohols

Significance

The design of a new chiral bishydroxamic acid ligand has resulted in its excellent utility in vanadium-catalyzed asymmetric epoxidation of alcohols. Cumene hydroperoxide is used as the epoxidizing agent and epoxidation can occur with as low as 0.5-1 mol% catalyst loadings at room temperature. Both trans and cis homoallylic alcohols can be epoxidized in excellent yields and enantioselectivities. Extension of this catalyst system to the kinetic resolution of homoallylic alcohols produced highly enantiopure starting alcohols and epoxy alcohols.