Asymmetric Synthesis of Organoelement Analogues of Natural Products; Part 12: General Method for the Asymmetric Synthesis of Fluorine-Containing Phenylalanines and α-Methyl(phenyl)alanines via Alkylation of the Chiral Nickel(II) Schiff's Base Complexes of Glycine and Alanine

Abstract

Nickel(II) complexes of Schiffs bases derived from (S)-o-[(N-benzyl]prolyl)amino]benzophenone [N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide] (BBP) and glycine or alanine have been used for asymmetric synthesis of fluoro (S)-phenylalanines and (S)-α-methyl(phenyl)alanines. Large selectivity (>90%) is observed for the alkylation of both complexes.