ASYMMETRIC-SYNTHESIS OF ORGANOELEMENT ANALOGS OF NATURAL-PRODUCTS .12. GENERAL-METHOD FOR THE ASYMMETRIC-SYNTHESIS OF FLUORINE-CONTAINING PHENYLALANINES AND ALPHA-METHYL(PHENYL)ALANINES VIA ALKYLATION OF THE CHIRAL NICKEL(II) SCHIFF-BASE COMPLEXES OF GLYCINE AND ALANINE

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)-alpha-methyl(phenyl)alanines. Large se...

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Published inSynthesis (Stuttgart) no. 1; pp. 117 - 120
Main Authors KUKHAR, VP, BELOKON, YN, SOLOSHONOK, VA, SVISTUNOVA, NY, ROZHENKO, AB, KUZMINA, NA
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.01.1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RESOLUTION
ALPHA-AMINO-ACIDS
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Summary: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)-alpha-methyl(phenyl)alanines. Large selectivity (> 90 %) is observed for the alkylation of both complexes 1 a and 1 b. The optically pure fluoro phenylalanines are obtained after the alkylated diastereoisomeric complexes had been separated on silica gel and hydrolyzed with aqueous hydrogen chloride.
ISSN:0039-7881