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Imine Anions Derived from 2° Allylic Amines

Robert M. K. Carlson, D. W. Hewetson, Martin Deeg, G. R. Mix, T. L. Liu

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Abstract

The application of allylic carbanions to organic synthesis is extensive2,3 and among the numerous variations are the generation and use of heteroallylic dianions. Noteworthy in this useful option is the ability of sulfide (−Sθ) to stabilize a developing adjacent carbanion,4,5 while alkoxide (−0θ) uniquely directs carbanion formation to a distal allylic position (Scheme I).6,7 We now wish to report that under conditions typically used for hetero allylic dianion formation 2° allylic amides provide a third reaction pathway for this structural entity by isomerizing to the resonance-stabilized imine anions (Scheme I).8,9 This overall conversion (presumably through an intermediate dianion) represents a heretofore unknown isomerization process that provides an alternative method for the generation of synthetically useful enolate equivalents.10

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The application of allylic carbanions to organic synthesis is extensive2,3 and among the numerous variations are the generation and use of heteroallylic dianions. Noteworthy in this useful option is the ability of sulfide (−Sθ) to stabilize a developing adjacent carbanion,4,5 while alkoxide (−0θ) uniquely directs carbanion formation to a distal allylic position (Scheme I).6,7 We now wish to report that under conditions typically used for hetero allylic dianion formation 2° allylic amides provide a third reaction pathway for this structural entity by isomerizing to the resonance-stabilized imine anions (Scheme I).8,9 This overall conversion (presumably through an intermediate dianion) represents a heretofore unknown isomerization process that provides an alternative method for the generation of synthetically useful enolate equivalents.10

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Available abstract

The application of allylic carbanions to organic synthesis is extensive2,3 and among the numerous variations are the generation and use of heteroallylic dianions. Noteworthy in this useful option is the ability of sulfide (−Sθ) to stabilize a developing adjacent carbanion,4,5 while alkoxide (−0θ) uniquely directs carbanion formation to a distal allylic position (Scheme I).6,7 We now wish to report that under conditions typically used for hetero allylic dianion formation 2° allylic amides provide a third reaction pathway for this structural entity by isomerizing to the resonance-stabilized imine anions (Scheme I).8,9 This overall conversion (presumably through an intermediate dianion) represents a heretofore unknown isomerization process that provides an alternative method for the generation of synthetically useful enolate equivalents.10

Key concepts: Carbanion, Allylic rearrangement, Chemistry, Imine, Isomerization, Sulfide, Medicinal chemistry, Organic chemistry

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