Asymmetric synthesis of amino acids by Cr(II) complexes of natural amino acids

Abstract

Stoichiometric reduction of the C,N double bond of oxime precursors of α-amino acids was performed in aqueous media by Cr(II) complexes of natural amino acids. The reduction of oximes of α-ketophenylacetic, α-keto-β-phenylpropionic and α-ketopropionic acids proceeded up to >90% conversion and 2–30% enantiomeric excess. 1:2 complexes of Cr(II) with l-alanine, l-valine, l-aspartic acid, l-histidine and l-phenylalanine were used as reducing agents. The reduction of α-(oximino)phenylacetic acid showed increasing e.e. (and decreasing conversion) with increasing temperature.