Amination of Optically Active Azaallylic Anions†‡

The reaction of azaallylic anions with ethyl N-[4-nitrobenzenesulfonyl)oxy]carbamate in the presence of a base gives a mixture of an alpha-amino ketone derivative with a slight preference for the (S) enantiomer and of an alpha-hydrazino ketone derivative as by-product; the same azaenolates react with bis(tert-butoxycarbonyl)diazene giving the analogous alpha-hydrazino ketone derivative, with a slight preference for the (R) enantiomer.