title: Chemical dynamic kinetic resolution and S/R interconversion of unprotected α-amino acids.
abstract: Reported herein is the first purely chemical method for the dynamic kinetic resolution (DKR) of unprotected racemic α-amino acids (α-AAs), a method which can rival the economic efficiency of the enzymatic reactions. The DKR reaction principle can be readily applied for S/R interconversions of α-AAs, the methodological versatility of which is unmatched by biocatalytic approaches. The presented process features a virtually complete stereochemical outcome, fully recyclable source of chirality, and operationally simple and convenient reaction conditions, thus allowing its ready scalability. A quite unique and novel mode of the thermodynamic control over the stereochemical outcome, including an exciting interplay between axial, helical, and central elements of chirality is proposed.
authors.affiliation: Hamari Chemicals Ltd. 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024 (Japan).
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Takeda
authors.forename: Akie
authors.initials: A
authors.lastname: Kawamura
authors.forename: Aki
authors.initials: A
authors.lastname: Kawashima
authors.forename: Tatsunori
authors.initials: T
authors.lastname: Sato
authors.forename: Hiroki
authors.initials: H
authors.lastname: Moriwaki
authors.forename: Kunisuke
authors.initials: K
authors.lastname: Izawa
authors.forename: Kenichi
authors.initials: K
authors.lastname: Akaji
authors.forename: Shuni
authors.initials: S
authors.lastname: Wang
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids
keywords: amino acids; chirality; diastereoselectivity; kinetic resolution; nickel