Modified aza-claisen rearrangement: Generation and isomerization of allyl enammonium salts |
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Authors: | John C Gilbert KPA Senaratne |
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Institution: | Department of Chemistry The University of Texas at Austin Austin, TX 78712 USA |
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Abstract: | Base-promoted reaction of ketones and diethyl (diazomethyl)phosphonate in the presence of allylic amines affords allylic enamines in good yields. These enamines undergo 3,3]-sigmatropic rearrangement upon alkylation and heating at 80°C to iminium salts which can be hydrolysed to aldehydes. The procedure allows generation of quaternary carbon centers under mild reaction conditions. |
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