Premium
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) -
Deschenaux Robert,
Bernauer Klaus
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670203
Subject(s) - chemistry , transamination , stereoselectivity , schiff base , ligand (biochemistry) , alanine , stereochemistry , enantiomer , pyridine , valine , amino acid , metal , copper , pyridoxamine , leucine , medicinal chemistry , organic chemistry , catalysis , pyridoxal , receptor , biochemistry , phosphate
Optically active alanine, valine and leucine were obtained by a transamination reaction between pyridoxamine and the corresponding α‐keto acid in the presence of a Cu 2+ ‐complex with the tridentate ligand 2,6‐bis[(3 S )‐3‐phenykl‐2‐azabutyl]pyridine. In each case the amino acid with ( R )‐configuration was formed preferentially, and the maximum 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 Cu 2+ ‐ketimine‐ligand complex.