NHC-catalyzed Reactions of Aryloxyacetaldehydes: a Domino Elimination/conjugate Addition/acylation Process for the Synthesis of Substituted Coumarins

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2008 Dec 4

PMID 19049403

Citations 16

Authors

Eric M Phillips

Manabu Wadamoto

Howard S Roth

Andrew W Ott

Karl A Scheidt

Affiliations

Soon will be listed here.

Abstract

N-heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4-dihydrocoumarins. The reaction proceeds through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.

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