Dirhodium Carboxylates Catalyzed Enantioselective Coupling Reactions of α-Diazophosphonates, Anilines, and Electron-Deficient Aldehydes

Dirhodium Carboxylates Catalyzed Enantioselective Coupling Reactions of α-Diazophosphonates, Anilines, and Electron-Deficient Aldehydes

Chiral dirhodium carboxylate complexes ([Rh2(S‐PTAD)4] or [Rh2(S‐PTTL)4], see scheme) efficiently catalyze asymmetric three‐component coupling reactions of α‐diazophosphonates, anilines, and electron‐deficient aldehydes to give α‐amino‐β‐hydroxyphosphonates. The high level of enantiocontrol provides...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-11, Vol.51 (45), p.11376-11380
Hauptverfasser: Zhou, Cong-Ying, Wang, Jing-Cui, Wei, Jinhu, Xu, Zhen-Jiang, Guo, Zhen, Low, Kam-Hung, Che, Chi-Ming
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Aniline Compounds - chemistry
asymmetric catalysis
Azo Compounds - chemistry
carbenoids
Carboxylic Acids - chemical synthesis
Carboxylic Acids - chemistry
Catalysis
diazo compounds
Molecular Structure
Organophosphonates - chemistry
rhodium
Rhodium - chemistry
Stereoisomerism
ylides
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Zusammenfassung:Chiral dirhodium carboxylate complexes ([Rh2(S‐PTAD)4] or [Rh2(S‐PTTL)4], see scheme) efficiently catalyze asymmetric three‐component coupling reactions of α‐diazophosphonates, anilines, and electron‐deficient aldehydes to give α‐amino‐β‐hydroxyphosphonates. The high level of enantiocontrol provides evidence for the intermediacy of metal‐bound ammonium ylide in the product‐forming step.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201206551