New chiral NiII complexes of Schiff’s bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids

Abstract: New modified chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(2-chlorobenzyl)pyrrolidine-2-carboxamide (2-CBPB) and (S)-N-(2-benzoylphenyl)-1-(3,4-dimethylbenzyl)pyrrolidine-2-carboxamide (3,4-DMBPB) and their NiII complexes of Schiff’s base with glycine and alanine have been synthesized and tested in asymmetric C-alkylation and aldol condensation reactions of amino acid moieties. The tests proved that both new auxiliaries were efficient with the ee’s of the final amino acids as high as 98% even in case of α-methyl-α-amino acid synthesis. [Copyright &y& Elsevier]