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Synthesis 1993; 1993(1): 117-120
DOI: 10.1055/s-1993-25812
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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

Valeri P. Kukhar* , Yuri N. Belokon, Vadim A. Soloshonok, Nataly Yu. Svistunova, Alexander B. Rozhenko, Nadezhda A. Kuz'mina
  • *Institute of Bioorganic Chemistry and Oil Chemistry of the Ukrainian Academy of Sciences, 253 160 Kiev, Ukraine
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Publication Date:
17 September 2002 (online)

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Nickel(II) complexes of Schiff's 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 1a and 1b. The optically pure fluoro phenylalanines are obtained after the alkylated diastereoisomeric complexes had been separated on silica gel and hydrolyzed with aqueous hydrogen chloride.