Synthesis of Deuterated Enaminones with High Isotopic Fidelity.

The unexpected oxidation of nitrogenous heterocycles by aldehyde oxidase (AO) may be addressed by the substitution of deuterium for hydrogen adjacent to the heterocycle nitrogen atom. Enaminones are versatile intermediates in the synthesis of nitrogenous heterocycles. We report that heretofore inaccessible monodeuterated enaminones of the general structure RC(=O)CH=CDNMe2 may be synthesized from methyl ketones and DCO2Me with high isotopic fidelity and efficient utilization of deuterium.