Chiral Ketone-Catalyzed Asymmetric Epoxidation of Olefins

Michael Frohn; Yian Shi

doi:10.1055/s-2000-8715

Synthesis 2000; 2000(14): 1979-2000
DOI: 10.1055/s-2000-8715

review

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Chiral Ketone-Catalyzed Asymmetric Epoxidation of Olefins

Michael Frohn^* , Yian Shi

^*Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA; Fax +1(970)4 91 18 01; E-mail: yian@lamar.colostate.edu

Abstract

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Dioxiranes are remarkably versatile oxidizing agents that show encouraging potential for asymmetric synthesis, particularly asymmetric epoxidation of unfunctionalized olefins. This review outlines the recent development in this area. Discussions are focused on the structural requirements of the chiral ketone catalysts, how structural changes effect the reactivity and selectivity of the catalyst, reaction conditions, and transition states.

asymmetric epoxidation - chiral dioxirane - chiral ketone - epoxide - hydrogen peroxide - oxone - potassium peroxymonosulfate

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