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A C-H Insertion Approach to Functionalized Cyclopentenones

Youliang Wang, Maxence Zarca, Liu-Zhu Gong and Liming Zhang*

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States, Email: zhangchem.ucsb.edu

Y. Wang, M. Zarca, L.-Z. Gong, L. Zhang, J. Am. Chem. Soc., 2016, 138, 7516-7519.

DOI: 10.1021/jacs.6b04297 (free Supporting Information)


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Abstract

A Au-catalyzed C-H insertion affords 2-bromocyclopent-2-en-1-ones from alkynone substrates with broad scope and synthetically desirable diastereoselectivities. The proposed key intermediate capable of the observed insertion into unactivated C–H bonds is a fully functionalized gold vinylidene.

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Key Words

cyclopentenones


ID: J48-Y2016