Tetrahedron

The Thionium/N-Acyliminium Ion Cyclization Cascade as a Strategy for the Synthesis of Azapolycyclic Ring Systems

A Padwa, AG Waterson

Index: Padwa, Albert; Waterson, Alex G. Tetrahedron, 2000 , vol. 56, # 52 p. 10159 - 10173

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Citation Number: 44

Abstract

A series of amidosulfoxides were prepared by the addition of thiophenol to the appropriate alkenoic acid π-bond, and this was followed by reaction of the in situ generated acyl chloride with 3, 4-dimethoxyphenethyl amine. The silicon-induced Pummerer reaction of these amidosulfoxides was carried out using 1-(dimethyl-tert-butylsiloxy)-1-methoxyethylene in dry acetonitrile in the presence of a catalytic amount of ZnI2 and led to the very clean ...