Fluoride-Mediated α-Selective 1,6-Conjugate Addition of Allenic Esters to p-Quinone Methides.

J Org Chem

Academy of Scientific and Innovative Research , New Delhi 110001 , India.

Published: August 2018


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Article Abstract

An efficient and expedient fluoride-mediated α-selective 1,6-conjugate addition of allenic esters to para-quinone methides has been developed. The reaction exhibited an excellent substrate scope, and a wide range of α-diarylmethylated allenic esters were obtained in good to excellent yields. It was further shown that the strategy could be extended to isatin-derived quinone methides yielding allenic esters containing 3,3-disubstituted oxindoles. The tert-butyl ester of α-diarylmethylated allenoate was effectively converted into γ-butenolide through a Au/Ag catalyzed cyclization strategy.

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http://dx.doi.org/10.1021/acs.joc.8b01074DOI Listing

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