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Silver(I)-Catalyzed Ring-Contractive Rearrangement: A New Entry to 5-Alkylidene-2-cyclopentenones

Liang Zhao, Jinlian Wang, Hongyan Zheng, Yun Li, Ke Yang, Bin Cheng, Xiaojie Jin, Xiaojun Yao and Hongbin Zhai*

*State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China, Email: zhaihlzu.edu.cn

L. Zhao, J. Wang, H. Zheng, Y. Li, K. Yang, B. Cheng, X. Jin, X. Yao, H. Zhai, Org. Lett., 2014, 16, 6378-6381.

DOI: 10.1021/ol503176y (free Supporting Information)


Abstract

A novel AgOTf-catalyzed ring-contractive rearrangement of 5-substituted 6-diazo-2-cyclohexenones provides a new and efficient access to 5-alkylidene-2-cyclopentenones. The reaction proceeds through metal-carbenoid formation followed by endocyclic allyl [1,2] migration with excellent stereoselectivity and broad substrate scope.

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proposed mechanism



Key Words

cyclopentenones


ID: J54-Y2014