title: 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.
abstract: 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.
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Deng
authors.forename: Xiang-Ping
authors.initials: XP
authors.lastname: Hu
authors.forename: Jia-Di
authors.initials: JD
authors.lastname: Huang
authors.forename: Sai-Bo
authors.initials: SB
authors.lastname: Yu
authors.forename: Dao-Yong
authors.initials: DY
authors.lastname: Wang
authors.forename: Zheng-Chao
authors.initials: ZC
authors.lastname: Duan
authors.forename: Zhuo
authors.initials: Z
authors.lastname: Zheng
mesh_terms: 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
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D004952:Esters; D007098:Imino Acids; D008024:Ligands; D010797:Phthalimides; D003300:Copper