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A Highly Regio- and Stereoselective Syntheses of α-Halo Enamides, Vinyl Thioethers, and Vinyl Ethers with Aqueous Hydrogen Halide in Two-Phase Systems

Wei Cao, Ping Chen, Liang Wang, Hao Wen, Yu Liu, Wanshu Wang and Yu Tang*

*Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Yushan Road, Qingdao 266003, P. R. China, Email: tangyuouc.edu.cn

W. Cao, P. Chen, L. Wang, H. Wen, Y. Liu, W. Wang, Y. Tang, Org. Lett., 2018, 20, 4507-4511.

DOI: 10.1021/acs.orglett.8b01809 (free Supporting Information)


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Abstract

A metal-free regio- and stereoselective method provides (E)-configured α-halo enamides, vinyl thioethers, and vinyl ethers using aqueous HX (X = F, Cl, Br, I). The method offers high functional group compatibility and regio- and stereoselectivity, mild conditions, high efficiency, and rapid transformation. Additionally, methods for the (E)- to (Z)-isomerization are described.

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Key Words

vinyl chlorides


ID: J54-Y2018