Download PDF
Synthesis 1993; 1993(1): 117-120
DOI: 10.1055/s-1993-25812
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >