Stereoselectivity in reactions of metal complexes. VII. Asymmetric synthesis of amino acids by metal ion-promoted transamination
Author(s)
Date issued
1983
In
Helv. Chim. Acta
Vol
7
No
66
From page
2049
To page
58
Subjects
asym synthesis amino acid phenylalanine asym synthesis phenylpyruvic acid condensation pyridoxamine kinetics keto acid condensation pyridoxamine isomerization copper ketimine complex transamination asym synthesis amino acid
Abstract
Enantioselective synthesis of phenylalanine was performed by reacting phenylpyruvic acid with pyridoxamine followed by ketimine-aldimine isomerization of the resulting Schiff base catalyzed by an optically active copper(II)-complex. UV and CD measurements showed that the enantiomeric excess strongly depends on the reaction conditions and on the reaction time and in favorable cases it reacted values of 80%. The selectivity of the reaction is discussed on the basis of possible structures of the intermediate mixed ligand complex. [on SciFinder(R)]
Publication type
journal article