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

Bin Wang, O. Andrea Wong, Mei-Xin Zhao and Yian Shi*

*Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, Email: yianlamar.colostate.edu

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

DOI: 10.1021/jo801576k (free Supporting Information)


Abstract

Up to 88% ee has been achieved for asymmetric epoxidation of 1,1-disubstituted terminal olefins using a chiral lactam ketone as catalyst. A planar transition state is likely to be a major reaction pathway.


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proposed transition state



An Efficient Catalytic Asymmetric Epoxidation Method

Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc., 1997, 119, 11224-11235.

Highly Enantioselective Epoxidation of cis-Olefins by Chiral Dioxirane

Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc., 1997, 119, 11224-11235.


Key Words

Epoxides, Organocatalysis, Oxone, Shi Epoxidation


ID: J42-Y2008-3660