Enantioselective synthesis of epoxides: sharpless epoxidation of alkenylsilanols

TH Chan, LM Chen, D Wang

Index: Chan, T. H.; Chen, L. M.; Wang, D. Journal of the Chemical Society, Chemical Communications, 1988 ,  # 19  p. 1280 - 1281

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Abstract

The Sharpless epoxidationl--3 has been hailed as one of the milestones in organic chemistry. The reaction gives chiral epoxides with predictable stereochemistry and high enan- tiometric purity. However, the reaction is limited to allylic alcohols. The hydroxy group plays a critical role in assembling the reactants together, thus accelerating the reaction as well as conferring high stereoselectivity. For simple alkenes without the pendant hydroxy group, Sharpless ...