Alkylation of Esters and Ketones with Nitroethylene
Buzby, Jennifer C.
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Nitroethylene is a potentially useful "+CH2CH2NH2" synthon that has not been widely used in conjugate addition reactions, due in part to its reputation for facile anionic polymerization. This paper reports a systematic study of the scope and limitations of the conjugate addition of ketone and esters to nitroethylene. Synthetically useful yields are reported for both esters and ketone lithium enolates of a variety of structural types. It was found that amonosubstituted ester and ketones enolates produced higher yields of addition products than their a-disubstituted counterparts. Substitution of the I3-carbon also improved yields in ester enolates.