Regioselective phosphorylation of α-N-alkylamino ketones

General preparative methods for regioselective functionalization of α-amino ketones with organophosphorus reagents were developed. Stable phosphorylated derivatives of all their prototropic forms (α-amino ketones, α-hydroxy imines, and β-hydroxy enamines) were obtained for the first time. The relative thermodynamic stability sequence of α-amino ketones was found to be reversed upon their phosphorylation: O-substituted forms were more stable than N-substituted ones, in contrast to the equilibrium between the prototropic isomers. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 288—293, February, 2006.