Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters: an efficient enantioselective synthesis of beta-aryl-gamma-amino acids.
A series of chiral beta-aryl-gamma-amino acid ester derivatives were synthesized in high enantioselectivities (93-97% ee) via the Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-alpha,beta-unsaturated carboxylic acid esters using highly modular chiral BoPhoz-type phosphine-aminophosphine ligands. The method has been applied successfully to the synthesis of several chiral pharmaceuticals including (R)-baclofen and (R)-rolipram with high enantioselectivities.
Deng
Jun
J
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Duan
Zheng-Chao
ZC
Huang
Jia-Di
JD
Hu
Xiang-Ping
XP
Wang
Dao-Yong
DY
Yu
Sai-Bo
SB
Xu
Xue-Feng
XF
Zheng
Zhuo
Z
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001418:Baclofen / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006865:Hydrogenation; D008024:Ligands; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D020889:Rolipram / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D004952:Esters; D008024:Ligands; D012238:Rhodium; D001418:Baclofen; D020889:Rolipram