title: Conversion of alpha,beta-unsaturated aldehydes into saturated esters: an Umpolung reaction catalyzed by nucleophilic carbenes.
abstract: N-Heterocyclic carbenes derived from benzimidazolium salts are effective catalysts for generating homoenolate species from alpha,beta-unsaturated aldehydes. These nucleophilic intermediates can be protonated, and the resulting activated carbonyl unit is trapped with an alcohol nucleophile, thereby promoting a highly efficient conversion of an alpha,beta-unsaturated aldehyde into a saturated ester. A kinetic resolution of secondary alcohols can be achieved using chiral imidazoylidene catalysts. [reaction: see text]
authors.affiliation: Department of Chemistry, Northwestern University, Evanston, IL 60208, USA.
authors.forename: Audrey
authors.initials: A
authors.lastname: Chan
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt