Abstract
A new class of catalysts of interfacial asymmetrical alkylation is suggested for the synthesis of α-amino acids — positively charged complexes of the transition metals Cu(II), Ni(II), and Pd(II). These complexes consist of several fragments, by variation of which the structure of the catalysts can readily be modified. The complexes are chiral on account of (S)proline derivatives contained in them as one of the fragments. The catalyst complexes (C) were used in the alkylation of amino acid fragments of Ni(II) complexes of the Schiff base of glycine with N-(2-pyridinecarbonyl)-o-aminobenzophenone (Ni-PBP-Gly) and the Schiff base of alanine with N-(2-pyridinecarbonyl)-o-aminobenzaldehyde (Ni-PBA-Ala) under interfacial conditions. After decomposition of the alkylated complexes, phenylalanine and α-methyl-phenylalanine were isolated with yields of 33–87% and optical purity (o.p.) from 3 to 21%, depending on the C used.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 126–134, January, 1991.
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Belokon', Y.N., Maleev, V.I., Videnskaya, S.O. et al. Transition metal complexes — A new class of catalysts of interfacial alkylation for the asymmetrical synthesis of α-amino acids. Russ Chem Bull 40, 110–118 (1991). https://doi.org/10.1007/BF00959641
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DOI: https://doi.org/10.1007/BF00959641