Hydroxy-directed, fluoride-catalyzed epoxide hydrosilylation for the synthesis of 1,4-diols.

A novel highly regioselective, fluoride-catalyzed hydrosilylation of ß-hydroxy epoxides has been developed. The reaction is modular and applicable to the synthesis of a broad range of 1,4-diols. Fluoride is crucial for two reasons: First, it promotes the formation of a silyl ether (which contains a Si-H bond) and, second, it enables ring opening by an intramolecular S(N)2 reaction through activation of the silane. The reaction can be performed under air.