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Abstract
The reaction of diethyl N-acetyl-N-methylphosphoramidate 1 with aldehyde in the presence of LDA at −70°C results in the formation of the unstable oxyanion 6 which undergoes intramolecular rearrangement involving migration of a phosphoryl group from nitrogen to oxygen affording an amide anion 8. Subsequent proton transfer in 8 followed by elimination of phosphate anion provides the respective α β-unsaturated N-methylcarboxamide 4. The formation of considerable amounts of diethyl N-methylphosphoramidate 5 is also always observed.