Enantioselective Rh-Catalyzed Hydrogenation of 3-Aryl-4-phosphonobutenoates with a P-Stereogenic BoPhoz-Type Ligand

Enantioselective Rh-Catalyzed Hydrogenation of 3-Aryl-4-phosphonobutenoates with a P-Stereogenic BoPhoz-Type Ligand

A series of chiral 3-aryl-4-phosphonobutyric acid esters were synthesized in high enantioselectivities (93−98% ee) via the Rh-catalyzed asymmetric hydrogenation of the corresponding 3-aryl-4-phosphonobutenoates using a P-stereogenic BoPhoz-type phosphine−aminophosphine ligand. The methodology has be...

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Veröffentlicht in:Journal of organic chemistry 2010-12, Vol.75 (23), p.8319-8321
Hauptverfasser: Duan, Zheng-Chao, Hu, Xiang-Ping, Zhang, Cheng, Zheng, Zhuo
Format: Artikel
Sprache:eng
Schlagworte:
Butyrates - chemistry
Catalysis
Chemistry
Esters
Exact sciences and technology
Hydrogenation
Ligands
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Organometalloidal and organometallic compounds
Organophosphonates - chemistry
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
P derivatives
Preparations and properties
Rhodium - chemistry
Stereoisomerism
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Zusammenfassung:A series of chiral 3-aryl-4-phosphonobutyric acid esters were synthesized in high enantioselectivities (93−98% ee) via the Rh-catalyzed asymmetric hydrogenation of the corresponding 3-aryl-4-phosphonobutenoates using a P-stereogenic BoPhoz-type phosphine−aminophosphine ligand. The methodology has been successfully applied to the asymmetric synthesis of a potential GABAB antagonist, (R)-phaclofen, in high enantioselectivity.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101849b