Enantioselective synthesis of epoxides via Sharpless epoxidation of alkenylsilanols

Abstract

Enantioselective synthesis of simple epoxides can be achieved by Sharpless epoxidation of alkenylsilanols followed by protodesilylation of the chiral epoxysilanols. The approach has been applied to the synthesis of frontalin.

Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds

“…In practice the idea does work. The silanol 1884 gave the epoxide 1885 in moderately high enantiomeric excess, and the reaction was used, with subsequent protodesilylation, for a synthesis of frontalin 1887 (Scheme ) . The same type of reaction was used in the kinetic resolution of a chiral silyl compound (Scheme ).…”

Utilization of Silanols in Transition Metal-Catalyzed Organic Synthesis

“…One representative example is the application of enantioselective Sharpless epoxidation reactions to alkenylsilanols instead of allylic alcohols that has been investigated since the first report by Chan . They found that a variety of alkenylsilanols 50 were applicable to Sharpless-type epoxidation to afford the corresponding epoxides substituted with hydroxysilyl groups 51 (Scheme ).…”