title: Asymmetric synthesis of α,β-diamino acid derivates via Mannich-type reactions of a chiral Ni(II) complex of glycine with N-tosyl imines.
abstract: A practical procedure composed of an asymmetric Mannich-type reaction between N-tosyl imine and a Ni(II) complex of glycine with (R)-o-[N-(N-benzylprolyl)amino]bezaophenone (BPB) as a chiral auxiliary catalyzed by Et(3)N in DMF to (R,2R,3S)-complexes, and decomposition of products with HCl to offer syn-(2R,3S)-α,β-diamino acids, was developed. Stereochemical mechanism of the Mannich reaction was proposed and supported by determining the absolute configuration of the product of the Mannich reaction relying on X-ray analysis. This two-step approach to amino acids was a general method and adapted to large-scale preparation.
authors.affiliation: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, 5 Xinmofan Road, Nanjing, 210009, China.
authors.forename: Guowei
authors.initials: G
authors.lastname: Song
authors.forename: Meihong
authors.initials: M
authors.lastname: Jin
authors.forename: Zhenjiang
authors.initials: Z
authors.lastname: Li
authors.forename: Pingkai
authors.initials: P
authors.lastname: Ouyang
mesh_terms: D000599:Amino Acids, Diamino / Q000138:chemical synthesis*; D005998:Glycine / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000599:Amino Acids, Diamino; D007097:Imines; D009532:Nickel; D005998:Glycine