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Two-step α-methylation via enamination with subsequent reduction was investigated on various methylene-containing heterocyclic carbonyl compounds including lactams, lactones, thiolactones etc. Outcomes or enamination with Bredereck’s reagent and DMF-DMA were compared. Optimal enamination and reduction protocols regarding solubility, reactivity and thermal stability of the substrates were elaborated. The construction of primary and secondary alkyl substituents through enaminone interaction with organometallic reagents was tested.
Frolov et al. (Mon,) studied this question.