The Development of Chiral, Nonracemic Dioxiranes for the Catalytic, Enantioselective Epoxidation of Alkenes

Scott E. Denmark; Zhicai Wu

doi:10.1055/s-1999-3123

Synlett 1999; 1999(S1): 847-859
DOI: 10.1055/s-1999-3123

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The Development of Chiral, Nonracemic Dioxiranes for the Catalytic, Enantioselective Epoxidation of Alkenes

Scott E. Denmark^* , Zhicai Wu

^*Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA; Fax +1(2 17)3 33 39 84; E-mail: denmark@scs.uiuc.edu

Abstract

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The catalytic, enantioselective epoxidation of unfunctionalized alkenes is a long-standing objective in organic synthesis. With the advent of dioxiranes as powerful oxygen atom transfer reagents that operate under neutral conditions, much attention has been directed to the development of chiral ketone precursors that can catalytically, differentiate the enantiotopic faces of simple alkenes. Advances in the design of various catalyst structures and the understanding of factors that influence high catalytic activity and stereoselectivity are presented.

epoxidation - epoxides - alkenes - dioxiranes - enantioselective catalysis

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