Stoichiometric reduction of the C,N double bond of oxime precursors of a-amino acids was performed in aqueous media by Cr(II) complexes of natural amino acids. The reduction of oximes of alpha-ketophenylacetic, alpha-keto-beta-phenylpropionic and alpha-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 alpha-(oximino)phenyl acetic acid showed increasing e.e. (and decreasing conversion) with increasing temperature.

Asymmetric synthesis of amino acids by Cr(II) complexes of natural amino acids / K., Micskei; O., Holczknecht; C., Hajdu; T., Patonay; V., Marchis; M., Meo; C., Zucchi; Palyi, Gyula. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - 682:(2003), pp. 143-148. [10.1016/S0022-328X(03)00775-7]

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

PALYI, Gyula
2003-01-01

Abstract

Stoichiometric reduction of the C,N double bond of oxime precursors of a-amino acids was performed in aqueous media by Cr(II) complexes of natural amino acids. The reduction of oximes of alpha-ketophenylacetic, alpha-keto-beta-phenylpropionic and alpha-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 alpha-(oximino)phenyl acetic acid showed increasing e.e. (and decreasing conversion) with increasing temperature.
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Asymmetric synthesis of amino acids by Cr(II) complexes of natural amino acids / K., Micskei; O., Holczknecht; C., Hajdu; T., Patonay; V., Marchis; M., Meo; C., Zucchi; Palyi, Gyula. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - 682:(2003), pp. 143-148. [10.1016/S0022-328X(03)00775-7]
K., Micskei; O., Holczknecht; C., Hajdu; T., Patonay; V., Marchis; M., Meo; C., Zucchi; Palyi, Gyula
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/306103
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