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Gold-Catalyzed Oxidative Cyclizations of {o-(Alkynyl)phenyl propargyl} Silyl Ether Derivatives Involving 1,2-Enynyl Migration: Synthesis of Functionalized 1H-Isochromenes and 2H-Pyrans

Jidong Zhao, Wei Xu, Xin Xie, Ning Sun, Xiangdong Li, Yuanhong Liu*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China, Email: yhliusioc.ac.cn

J. Zhao, W. Xu, X. Xie, N. Sun, X. Li, Y. Liu, Org. Lett., 2018, 20, 5461-5465.

DOI: 10.1021/acs.orglett.8b02380 (free Supporting Information)


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Abstract

Gold-catalyzed oxidative cyclizations of o-(alkynyl)phenyl propargyl ether derivatives enable a convenient synthesis of functionalized 1H-isochromene and 2H-pyran derivatives via highly regioselective oxidation, followed by 1,2-migration of an enynyl group and nucleophlic addition. Oxidative cleavage of the exocyclic double bond of the obtained 1H-isochromenes provides isocoumarins.

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Key Words

Isochromenes, Pyridine N-oxide derivatives


ID: J54-Y2018