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
- 1 January 1993
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1993 (01) , 117-120
- https://doi.org/10.1055/s-1993-25812
Abstract
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.Keywords
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