Reaction of dilithium derivatives of oximes with electrophiles. Regiospecific substitution of ketones

WG Kofron, MK Yeh

Index: Kofron,W.G.; Yeh,M.-K. Journal of Organic Chemistry, 1976 , vol. 41, # 3 p. 439 - 442

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Citation Number: 57

Abstract

Dilithium derivatives of ketoximes react with alkyl halides and carbonyl compounds to give a- substituted ox-imes. The position of substitution is governed by the configuration of the oxime. The intermediate monolithio ox-imes are configurationally stable, allowing successive substitution on the same carbon. Since no oxime exchange is observed with carbonyl compounds, directed aldol condensation is possible.