Abstract
Abstract Some fluorine-containing amino acids have been known to inactivate certain enzymes selectively and irreversibly. We have synthesized β-(polyfluoro ethyl)alanines and β-(trifluorovinyl)alanine from polyfluoroiodoethanes and acrylate. The synthetic schemes of β-(polyfluoroethyl)- alanines are shown below. Using similar procedures, we have also prepared β-(polyfluoroethyl)-β-methylalanines, CF 2 XCFX′CH(CH 3 )- CH(NH 2 )CO 2 H from polyfluoroiodoethanes and ethyl crotonate. β-(Trifluorovinyl)alanine was synthesized in a good yield from the ester of β-(dichlorotrifluoro ethyl)alanine as follows: The reactive trifluorovinyl group in the amino acid allows us to synthesize various kinds of fluorine- containing amino acids with a functional group through radical and ionic addition reactions. Some reactions of the ester of N-acetylated β-(trifluorovinyl)alanine with alkoxides (nucleophilic addition) and alcohols (radical addition) will be mentioned.
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