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Enantioselective [3 + 2] Cycloaddition Reaction of Ethynylethylene Carbonates with Malononitrile Enabled by Organo/Metal Cooperative Catalysis

Yu-Chen Zhang, Bo-Wen Zhang, Rui-Long Geng, Jin Song*

*Department of Chemistry, University of Science and Technology of China, Hefei 230026, China, Email: jillustc.edu.cn

Y.-C. Zhang, B.-W. Zhang, R.-L. Geng, J. Song, Org. Lett., 2018, 20, 7907-7911.

DOI: 10.1021/acs.orglett.8b03454 (free Supporting Information)



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Abstract

An organo/copper cooperative system enables a catalytic asymmetric decarboxylative [3 + 2] cycloaddition reaction of ethynylethylene carbonates with malononitrile to provide optically active polysubstituted dihydrofurans in good yields with high levels of enantioselectivities. The presence of the cyano group and the terminal alkynyl provides a wide scope for further structural transformations.

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proposed mechanism



Key Words

2,3-dihydrofurans


ID: J54-Y2018