Enantioselective Epoxidation of Conjugated cis-Enynes by Chiral Dioxirane

Christopher P. Burke and Yian Shi*
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523
J. Org. Chem., 2007, 72 (11), pp 4093–4097
DOI: 10.1021/jo070205r
Publication Date (Web): April 26, 2007
Copyright © 2007 American Chemical Society
*

 Corresponding author. Phone:  970-491-7424. Fax:  970-491-1801.

, yian@lamar.colostate.edu

Abstract

Abstract Image

This paper describes a highly chemo- and enantioselective epoxidation of conjugated cis-enynes using readily available glucose-derived ketone 2 as catalyst and Oxone as oxidant to form cis-propargyl epoxides in high ee's. The interaction between the alkyne group of the substrate and the oxazolidinone moiety of the ketone catalyst as well as the interactions between the substituents on enynes and the oxazolidinone moiety of the ketone catalyst are important for the stereodifferentiation.

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History

  • Published In Issue May 25, 2007
  • Received February 2, 2007

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