title: Synthesis of bis-α,α'-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine.
abstract: The Ni(II) complex derived from glycine Schiff base with (S)-N-(benzylprolyl)-2-aminobenzophenone can be effectively alkylated with α,ω-dibromide reagents to furnish the corresponding bis-alkylated products. This method presents a direct approach for the preparation of the corresponding bis-α,α'-amino acids with high biological importance. Heterogeneous (phase-transfer) as well as homogeneous conditions for the alkylation reactions have been investigated and the latter proved to be more efficient in terms of stereochemical outcome. In particular, alkylation of the glycine Schiff base Ni(II) complex with 1,3-dibromopropane followed by acid-catalysed hydrolysis of the resulting bis-alkylation product, allowed for the preparation of naturally occurring (2S,6S)-diaminopimelic acid in high overall yield.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zu chong zhi Road, Shanghai 201203, People's Republic of China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.forename: Daniel
authors.initials: D
authors.lastname: Houck
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Takeda
authors.forename: Hiroki
authors.initials: H
authors.lastname: Moriwaki
authors.forename: Tatsunori
authors.initials: T
authors.lastname: Sato
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001577:Benzophenones / Q000737:chemistry; D056831:Coordination Complexes / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001577:Benzophenones; D056831:Coordination Complexes; D012545:Schiff Bases; D009532:Nickel; D005998:Glycine