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Palladium-Catalyzed Cyclization-Heck Reaction of Allenamides: An Approach to 3-Methylene-5-phenyl-1,2,3,4-tetrahydropyridine Derivatives

Fachao Yan, Hanbing Liang, Jian Song, Jie Cui, Qing Liu, Sheng Liu, Ping Wang, Yunhui Dong* and Hui Liu*

*School of Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, P. R. China, Email: dyh651118126.com, huiliu1030sdut.edu.cn

F. Yan, H. Liang, J. Song, J. Cui, Q. Liu, S. Liu, P. Wang, Y. Dong, H. Liu, Org. Lett., 2017, 19, 86-89.

DOI: 10.1021/acs.orglett.6b03364 (free Supporting Information)


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Abstract

A palladium-catalyzed cyclization-Heck reaction of allenamides enables an efficient one-pot construction of functionalized 3-methylene-5-aryl-1,2,3,4-tetrahydropyridines. These compounds feature a nonconjugated diene, including one endo-enamine and one exocyclic double bond, which could be used for further transformation.

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proposed mechanism



Key Words

1,2,3,4-tetrahydropyridines


ID: J54-Y2017