Tetrahedron letters

Alkylation of ketone and ester lithium enolateswith nitroethylene

RJ Flintoft, JC Buzby, JA Tucker

Index: Flintoft, Rebecca J.; Buzby, Jennifer C.; Tucker, John A. Tetrahedron Letters, 1999 , vol. 40, # 24 p. 4485 - 4488

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Citation Number: 6

Abstract

Nitroethylene is a “+ CH2CH2NH2 “and “+ CH2CHO “synthon which has not beenwidely 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 ...