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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, Email: yianlamar.colostate.edu

C. P. Burke, Y. Shi, J. Org. Chem., 2007, 72, 4093-4097.

DOI: 10.1021/jo070205r (free Supporting Information)


Abstract

A highly chemo- and enantioselective epoxidation of conjugated cis-enynes using readily available glucose-derived ketones as catalysts and Oxone as oxidant forms cis-propargyl epoxides in high ee's.  The interaction between the alkyne substrate and the oxazolidinone moiety of the ketone catalyst are important for the stereodifferentiation.

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Asymmetric Epoxidation of 1,1-Disubstituted Terminal Olefins by Chiral Dioxirane via a Planar-like Transition State

B. Wang, O. A. Wong, M.-X. Zhao, Y. Shi, J. Org. Chem., 2008, 73, 9539-9543.


Key Words

Epoxides, Organocatalysis, Oxone, Shi Epoxidation


ID: J42-Y2007-1590