Stereoselectivity in reactions of metal complexes. VIII. Asymmetric synthesis of some amino acids by stereoselective transamination of aliphatic keto acids in mixed ligand copper(II)-Schiff-base complexes
Author(s)
Bernauer, Klaus
Date issued
1984
In
Helv. Chim. Acta
Vol
2
No
67
From page
373
To page
7
Subjects
asym synthesis amino acid stereoselective transamination keto acid pyridoxamine transamination keto acid cupric phenylazabutylpyridine complex promoter transamination
Abstract
Optically active alanine, valine and leucine were obtained by a transamination reaction between pyridoxamine and the corresponding ?-keto acid in the presence of a Cu2+-complex with the tridentate ligand 2,6-bis[(3S)-3-phenyl-2-azabutyl]pyridine. In each case the amino acid with (R)-configuration was formed preferentially, and the max. enantiomeric excesses were 54% (alanine), 48% (leucine) and 29% (valine). The stereoselectivity of the reaction is discussed in terms of the possible structure and the stability of the intermediate Cu2+-ketimine-ligand complex. [on SciFinder(R)]
Publication type
journal article