title: Chemical kinetic resolution of unprotected β-substituted β-amino acids using recyclable chiral ligands.
abstract: The first chemical method for resolution of N,C-unprotected β-amino acids was developed through enantioselective formation and disassembly of nickel(II) complexes under operationally convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled along with isolation of the target β-substituted-β-amino acids in good yields and excellent enantioselectivity. The method features a broad synthetic generality including β-aryl, β-heteroaryl, and β-alkyl-derived β-amino acids. The procedure is easily scaled up, and was used for the synthetically and economically advanced preparation of the anti-diabetic drug sitagliptin.
authors.affiliation: State Key Laboratory of Drug Research, CAS Key Laboratory of Receptor Research Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203 (P. R. China).
authors.forename: Shengbin
authors.initials: S
authors.lastname: Zhou
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.forename: Xia
authors.initials: X
authors.lastname: Chen
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification*; D002627:Chemistry, Physical; D007700:Kinetics; D008024:Ligands; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D008024:Ligands; D009532:Nickel
keywords: N ligands; amino acids; enantioselectivity; kinetic resolution; nickel