title: Protonation of Homoenolate Equivalents Generated by N-Heterocyclic Carbenes.
abstract: Homoenolate equivalents are generated by Lewis basic N-heterocyclic carbene catalysts and then protonated to generate efficiently saturated esters from unsaturated aldehydes. This reactivity is extended to the generation of β-acylvinyl anions from alkynyl aldehydes. The asymmetric protonation of a homoenolate equivalent generated from a β,β-disubstituted aldehyde can be accomplished with a chiral N-heterocyclic carbene.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA.
authors.forename: Brooks E
authors.initials: BE
authors.lastname: Maki
authors.forename: Audrey
authors.initials: A
authors.lastname: Chan
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt