Alkylation of Ketone and Ester Enolates by Nitroethylene
Flintoft, Rebecca J.
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The successful Michael addition ofnitroethylene to various lithium ester and ketone enolates is reported. Higher and more easily purified yields are reported for the adducts of ester enolates than for the adducts of ketone enolates. In addition, a-monosubstituted ester and ketone enolates were found to react in higher yield with nitroethylene than did their a-disubstituted counterparts. The significance of these reactions is reinforced by the common misconception that nitroethylene is too unstable to produce high yields in nucleophilic addition reactions. Furthermore, these reactions support the assertion that nitroethylene may have synthetic utility as a "+CH2CH2NH2" synthon.