Protonation of Homoenolate Equivalents Generated by N-Heterocyclic Carbenes
- 18 March 2008
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2008 (8) , 1306-1315
- https://doi.org/10.1055/s-2008-1072516
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.Keywords
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