Abstract
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.
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