N-Heterocyclic Carbene-Catalyzed Reaction of Chalcones and Enals via Homoenolate: an Efficient Synthesis of 1,3,4-Trisubstituted Cyclopentenes

Nair, Vijay; Vellalath, Sreekumar; Poonoth, Manojkumar; Suresh, Eringathodi

doi:10.1021/ja0625677

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N-Heterocyclic Carbene-Catalyzed Reaction of Chalcones and Enals via Homoenolate: an Efficient Synthesis of 1,3,4-Trisubstituted Cyclopentenes

Published in Journal of the American Chemical Society • Jun 20, 2006

Authors:

Vijay Nair

Sreekumar Vellalath

Manojkumar Poonoth

Abstract

Nucleophilic heterocyclic carbene-catalyzed cyclopentannulation of enals and chalcones via homoenolate has been observed for the first time. Serendipitously, the reaction lead to a very efficient synthesis of 3,4-trans-disubstituted-1-aryl cyclopentenes instead of the expected cyclopentanones. The s...

Subject

Chemistry

Cyclopentene

Carbene

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