Regioselective phosphorylation of α-N-alkylamino ketones

Research paper by S. E. Pipko, Yu. V. Balitsky, N. V. Simurova, A. D. Sinitsa

Indexed on: 01 Feb '06Published on: 01 Feb '06Published in: Russian Chemical Bulletin


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.