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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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 288—293, February, 2006.
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Pipko, S.E., Balitsky, Y.V., Simurova, N.V. et al. Regioselective phosphorylation of α-N-alkylamino ketones. Russ Chem Bull 55, 295–300 (2006). https://doi.org/10.1007/s11172-006-0251-x
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DOI: https://doi.org/10.1007/s11172-006-0251-x