Tetrahedron letters

Modified aza-claisen rearrangement: Generation and isomerization of allyl enammonium salts

JC Gilbert, KPA Senaratne

Index: Gilbert, John C.; Senaratne, K. P. A. Tetrahedron Letters, 1984 , vol. 25, # 22 p. 2303 - 2306

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Citation Number: 18

Abstract

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.