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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:

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

DOI: 10.1021/jo070205r (free Supporting Information)


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.

see article for more examples

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