Enantioselective synthesis of beta-aryl-gamma-amino acid derivatives via Cu-catalyzed asymmetric 1,4-reductions of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters.
A series of chiral beta-aryl-substituted gamma-amino butyric acid derivatives were synthesized in good enantioselectivities via the Cu-catalyzed asymmetric conjugate reduction of gamma-phthalimido-alpha,beta-unsaturated carboxylic acid esters using Cu(OAc)2 x H2O as a catalyst precursor, (S)-BINAP as a ligand, PMHS as a hydride source, and t-BuOH as an additive. The methodology has been applied successfully to the enantioselective synthesis of a chiral pharmaceutical, (R)-baclofen.
Deng
Jun
J
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Hu
Xiang-Ping
XP
Huang
Jia-Di
JD
Yu
Sai-Bo
SB
Wang
Dao-Yong
DY
Duan
Zheng-Chao
ZC
Zheng
Zhuo
Z
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D007098:Imino Acids / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D002264:Carboxylic Acids; D004952:Esters; D007098:Imino Acids; D008024:Ligands; D010797:Phthalimides; D003300:Copper