Abstract
Several recent developments in our laboratories have made it possible to elaborate a general method for preparing optically pure fluorine containing α-amino acids starting from a Ni(II)-complex ( 1) of a Schiff's base derived from (S)-o-[(benzylpropyl)amino]-benzophenone (BBP) and glycine or alanine. ▪ Alkylation of ( 1) with fluorine-substituted benzyl halides and aldehyde condensation result, respectively, in fluorine-containing S-Phe and its α-methyl derivatives, 2R,3S-, 2S,3R-, 2R,3R-PhSer and 2S,3S-β-perfluoroalkyl Ser in good chemical and optical yields. Simplicity of the synthetic procedure, ease of recovery of the chiral auxiliary (BBP), and the possibility of obtaining optically pure fluorine containing amino acids make this method attractive. The influence of fluorine atoms or fluorine containing groups and reaction conditions on the stereochemical results in the reactions of this type will be discussed.
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