MilliporeSigma
  • Home
  • Search Results
  • Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of α-amino acids.

Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of α-amino acids.

Amino acids (2013-09-18)
Alexander E Sorochinsky, José Luis Aceña, Hiroki Moriwaki, Tatsunori Sato, Vadim Soloshonok
ABSTRACT

This review provides a comprehensive treatment of literature data dealing with asymmetric synthesis of α-amino-β-hydroxy and α,β-diamino acids via homologation of chiral Ni(II) complexes of glycine Schiff bases using aldol and Mannich-type reactions. These reactions proceed with synthetically useful chemical yields and thermodynamically controlled stereoselectivity and allow direct introduction of two stereogenic centers in a single operation with predictable stereochemical outcome. Furthermore, new application of Ni(II) complexes of α-amino acids Schiff bases for deracemization of racemic α-amino acids and (S) to (R) interconversion providing additional synthetic opportunities for preparation of enantiomerically pure α-amino acids, is also reviewed. Origin of observed diastereo-/enantioselectivity in the aldol, Mannich-type and deracemization reactions, generality and limitations of these methodologies are critically discussed.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Glycine, 99%, FCC
SAFC
Glycine
Sigma-Aldrich
Glycine, tested according to Ph. Eur.
Sigma-Aldrich
Glycine, BioUltra, for molecular biology, ≥99.0% (NT)
Sigma-Aldrich
Glycine, ACS reagent, ≥98.5%
Sigma-Aldrich
Glycine, ReagentPlus®, ≥99% (HPLC)
Sigma-Aldrich
Glycine, BioXtra, ≥99% (titration)
Sigma-Aldrich
Glycine, suitable for electrophoresis, ≥99%
Sigma-Aldrich
Glycine, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, ≥98.5%
Supelco
Glycine, Pharmaceutical Secondary Standard; Certified Reference Material
Glycine, European Pharmacopoeia (EP) Reference Standard
USP
Glycine, United States Pharmacopeia (USP) Reference Standard