Alkylation of ketone and ester lithium enolates with nitroethylene

Article abstract of DOI:10.1016/S0040-4039(99)00814-X

Nitroethylene is a '⁺CH₂CH₂NH₂' and '⁺CH₂CHO' synthon which has not been widely used in conjugate addition reactions, due in part to its reputation for facile anionic polymerization. In the present report, we describe the first systematic study of the scope and limitations of the conjugate addition of ketone and ester enolates to nitroethylene. Synthetically useful yields are obtained for ketone and ester enolates of a variety of structural types.