Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones.

Chemistry

The College of Chemistry, the State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Wiejin Road 94#, Tianjin, 300071, P. R. China.

Published: May 2016


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Article Abstract

Mutual cooperation in the formal allyl alcohol nucleophilic substitution reaction and hydration of an alkyne has been utilized in the presence of a gold catalyst to give a series of γ-functionalized ketones with high to excellent yields. This reaction actually involved an intramolecular O-H insertion cyclization of an alkyne to form the dihydrofuran intermediate, which was followed by the nucleophilic addition ring-opening of a dihydrofuran to give the target compound.

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http://dx.doi.org/10.1002/chem.201600248DOI Listing

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