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 been successfully applied to the asymmetric synthesis of a potential GABA(B) antagonist, (R)-phaclofen, in high enantioselectivity.
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Zheng-Chao
ZC
Duan
Xiang-Ping
XP
Hu
Cheng
C
Zhang
Zhuo
Z
Zheng
D002087:Butyrates / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D006865:Hydrogenation; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D002087:Butyrates; D004952:Esters; D008024:Ligands; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D012238:Rhodium