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Reaction Of Linear Push-Pull Enamines At The β′-Position

A. Kostyuk, D. Volochnyuk, Dmitriy A. Sibgatulin
Published 2008 · Chemistry

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Enamine tautomerism is often the main cause of regio-selectivity problems in the chemistry of enamines derived from -ketones. Linear push-pull tertiary enamines featuring a methyl -(methylene) group at the α-position do not experience such tau-to-merism; nevertheless, a number of reactions proceed with participation of the methyl (methylene) group. It was our objective to analyze all known reactions of this type and show their high synthetic potential. 1 Introduction 2 Electrophilic Functionalization of Preformed Lithiated or Silylated Enamines 3 Uncatalyzed Reactions of Monoelectrophilic Reagents at the Methyl (Methylene) Group 4 Reactions Proceeding at Both the β- and β′-Carbon of the Enamine 5 Reactions Proceeding at the α-Methyl (Methylene) Group and β-Functional Group 6 Conclusion

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