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Stereoselectivity in reactions of metal complexes VII. Asymmetric synthesis of amino acids by metal ion-promoted transamination

✍ Scribed by Klaus Bernauer; Robert Deschenaux; Toshiaki Taura

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
499 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Enantioselective synthesis of phenylalanine was performed by reacting phenylpyruvic acid with pyridoxamine followed by ketimine‐aldimine isomerization of the Schiff base formed catalyzed by an optically active copper (II)‐complex. By UV and CD measurements it was shown that the enantiomeric excess strongly depends on the reaction conditions and on the reaction time. In favorable cases it reached values up to 80%. The selectivity of the reaction is discussed on the basis of possible structures of the intermediate mixed ligand complex.

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