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

Article abstract of DOI:10.1002/hlca.19840670203

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 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 maximum enantiomeric excesses were 54percent (alanine), 48percent (leucine) and 29percent (valine).The stereoselectivity of the reaction is discussed in terms of the possible structure and the stability of the intermediate Cu²⁺-ketimine-ligand complex.