Sharpless epoxidation of the alkenylsilanol (6) followed by protodesilylation gave styrene oxide with high enantiomeric excess.

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.

Enantioselective Synthesis Using Organosilicon Compounds -(22 refs.). -(CHAN, T. H.; WANG, D.; PELLON, P.; LAMOTHE, S.; WIE, Z. Y.; LI, L. H.; CHEN, L. M.; 9 (1990) 344-355; Edited by Bassindale, A. R.; Gaspar, P. P.; R. Soc. Chem., Cambridge, UK; EN)

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