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