3 years ago

[ASAP] 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

[ASAP] 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
Yuanhong Liu, Wei Xu, Xin Xie, Ning Sun, Jidong Zhao, Xiangdong Li
A new and convenient strategy for the synthesis of functionalized 1H-isochromene and 2H-pyran derivatives based on gold-catalyzed oxidative cyclizations of o-(alkynyl)phenyl propargyl ether derivatives has been developed. The reaction proceeds via gold-catalyzed highly regioselective oxidation, followed by 1,2-migration of an enynyl group and nucleophlic addition. Isocoumarins were also constructed through oxidative cleavage of the exocyclic double bond of the obtained 1H-isochromenes.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.8b02380

DOI: 10.1021/acs.orglett.8b02380

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