SYNTHESIS OF ALPHA-AMINO-ACIDS BY ALKYLATION OF DIETHYL ACETAMIDOMALONATE IN THE PRESENCE OF PALLADIUM COMPLEXES

The use of diethyl acetamidomalonate (1a) and its sodium derivative (1b) as nucleophilic reagents toward olefins and diolefins via their Π-olefin-and Π-allyl-palladium complexes has been studied. In the presence of a palladium catalyst, 1, 3-dienes reacted with la to form linear 2, 7-alkadienyl derivatives as main products. With the same catalyst, diethyl allylacetamidomalonate was obtained by an intermolecular exchange reaction of the allyl groups of allyl acetate or allyl alcohol. Allylic derivatives of la were also obtained by the stoichiometric reaction of lb on isolated Π-allyl-palladium complexes. The analogous nucleophilic alkylation of monoolefins is also described. All these condensation products may be further subjected to hydrolysis and decarboxylation to give the corresponding α-amino acids. © 1979, American Chemical Society. All rights reserved. © 1979, American Chemical Society. All rights reserved.