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.
Original language | English (US) |
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Pages (from-to) | 1306-1315 |
Number of pages | 10 |
Journal | Synthesis |
Issue number | 8 |
DOIs | |
State | Published - Apr 17 2008 |
Keywords
- Asymmetric catalysis
- Carbenes
- Esters
- Protonations
- Umpolung
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry