Abstract
A new chiral synthon of the electrophilic glycine — the Ni(II) complex of the Schiff base of L-N-benzylprolylorthoaminobenzophenone with α-bromoglycine — was synthesized. The reaction of this complex with nucleophiles led to the isolation of complexes of L- and D-2-amino-2-dimethylaminoacetic acid, L- and D-2-amino-2-phenoxyacetic acid, 3,3-di(carbethoxy)alanine, and norleucine. The decomposition of the 3,3-di(carbethoxy)alanine and norleucine complexes led to the synthesis of L-aspartic acid and L-norleucine with the enantiomeric purity of 80 and 68% correspondingly.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1899–1902, August, 1989.
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Belokon, Y.N., Popkov, A.N., Chernoglazova, N.I. et al. New chiral synthon of electrophilic glycine and its reactions with metalloorganic, C-H, N-H, and O-H compounds for the asymmetric synthesis of α-substituted α-amino acids. Russ Chem Bull 38, 1744–1748 (1989). https://doi.org/10.1007/BF00956966
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DOI: https://doi.org/10.1007/BF00956966