Deamination of the amino acid fragment in imine metallacycles:: Unexpected synthesis of an NH-aldimine organometallic compound

We report that the action of Lewis bases, such as triphenylphosphine, pyridine, or trimethylamine, on imine metallacycles derived from amino acids leads to the formation of the first organometallic compound of an NH aldimine, a highly reactive organic species, and the corresponding alpha-ketoester, in a deamination reaction that mimics the metabolism of cc-amino acids. The synthesis of different cyclopalladated compounds by a reaction between palladium acetate and the Schiff bases 2,4,6-Me3C6H2CH = NCH(R-1)COOR2 (R-1 = CH2Ph, R-2 = Et and R-1 = Ph, R-2 = Me) is also reported.