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. 2006 Jul 12;128(27):8736-7.
doi: 10.1021/ja0625677.

N-heterocyclic carbene-catalyzed reaction of chalcones and enals via homoenolate: an efficient synthesis of 1,3,4-trisubstituted cyclopentenes

Vijay Nair  1 , Sreekumar Vellalath, Manojkumar Poonoth, Eringathodi Suresh
Affiliations

N-heterocyclic carbene-catalyzed reaction of chalcones and enals via homoenolate: an efficient synthesis of 1,3,4-trisubstituted cyclopentenes

Vijay Nair et al. J Am Chem Soc. .

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 strategy works well with thienylidene tetralone also, leading to the tricyclic cyclopentene derivative.

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