Tetrahedron

A convenient route to β-aryl-substituted cyclic enamines as key synthetic intermediates of sceletium and amaryllidaceae alkaloids

Y Matsumura, J Terauchi, T Yamamoto, T Konno…

Index: Matsumura, Yoshihiro; Terauchi, Jun; Yamamoto, Takashi; Konno, Takashi; Shono, Tatsuya Tetrahedron, 1993 , vol. 49, # 38 p. 8503 - 8512

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Abstract

Aryl groups were introduced into the position β to the nitrogen atom of cyclic amines by carrying out the anodic α-methoxylation of cyclic amine derivatives, the elimination of methanol from the oxidized products, the halomethoxylation of the resulting α, β-unsaturated cyclic amine derivatives, the replacement of the α-methoxy group with an aryl group, and the silver ion-promoted migration of the α-aryl group to the β-position, consecutively. This ...