Catalytic Intermolecular Aldehyde−Ketone Coupling via Acyl Phosphonates

Catalytic Intermolecular Aldehyde−Ketone Coupling via Acyl Phosphonates

The first catalytic intermolecular aldehyde−ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate−phosphate rearrangement. These anions readily react with activa...

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Veröffentlicht in:Journal of organic chemistry 2009-03, Vol.74 (5), p.2197-2199
Hauptverfasser: Demir, Ayhan S, Esiringü, lker, Göllü, Mehmet, Reis, Ömer
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Aliphatic compounds
Catalysis
Chemistry
Exact sciences and technology
Ketones - chemistry
Molecular Structure
Organic chemistry
Organophosphonates - chemistry
Preparations and properties
Stereoisomerism
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Zusammenfassung:The first catalytic intermolecular aldehyde−ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate−phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41−95% yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo8026627