Asymmetric synthesis of aspartic and α-methylaspartic acids via Ni(II) complexes with schiff bases of glycine and alanine and chiral carbonyl-containing reagents

Autor: Belokon', Yu. N., Tararov, V. I., Maleev, V. I., Motsishkite, S. M., Vitt, S. V., Chernoglazova, N. I., Savel'eva, T. F., Saporovskaya, M. B.
Zdroj: Russian Chemical Bulletin; July 1991, Vol. 40 Issue: 7 p1361-1365, 5p
Abstrakt: We propose a method for the synthesis of aspartic and a-methylaspartic acids by alkylation with ethyl bromoacetate of the a-carbon atom of the amino acid moiety in Ni(II) complexes of Schiff bases of glycine with (S)-2-[(N-benzylprolyl)amino]benzophenone and alanine with (S)-2-[(N-benzylprolyl)amino]-benzaldehyde, respectively. Attempts to synthesize a-methylaspartic acid by oxidative cleavage of the C=C bond to a COOH group in the complex of the Schiff base of a-allylalanine with (S)-2-[(N-benzylprolyl)amino]benzophenone were unsuccessful.
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