Work

Protonation of Homoenolate Equivalents Generated by N-Heterocyclic Carbenes

Year: 2008

Type: article

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.

Source: Synthesis

DOI: 10.1055/s-2008-1072516

Authors: Karl Scheidt, Brooks Maki, Audrey Chan

Institution: Northwestern University

Language: English

Topic: N-Heterocyclic Carbenes in Organic and Inorganic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Dow Chemical Company, National Cancer Institute, National Institute of General Medical Sciences

Awards: G219817190, G682315649