A series of highly acidic nucleophilic glycine equivalents, valuable for the preparation of unnatural a-amino acids via homologation approaches, have been developed.  These novel nucleophilic glycine equivalents are founded on the modular design of Ni(II) glycine Schiff Bases.  The increased acidity of the a-protons of the glycine moiety arises from the strategic introduction of trifluoromethyl group(s) into the benzophenone module of the nucleophilic glycine complexes.  The syntheses of the various trifluoromethyl containing glycine equivalents, as well as the previously unreported synthesis of the necessary trifluoromethylated amino-benzophenones, are described.  The reactivity of this series of glycine equivalents has been investigated by the evaluation of competitive reactions between the Ni(II) complexed glycine equivalents containing a 2-aminobenzophenone, a 2-amino-4'-(trifluoromethyl)-benzophenone, or a 2-amino-3',5'-bis(trifluoromethyl)-benzophenone moiety under kinetic and thermodynamic reaction conditions.

Synthesis and evaluation of a new generation of highly acidic nucleophilic glycine equivalents for the preparation of unnatural α-amino acids

245th National Meeting (2013)

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