Prototype Pictet-Spengler reactions catalyzed by superacids. Involvement of dicationic superelectrophiles

A Yokoyama, T Ohwada, K Shudo

Index: Yokoyama, Akihiro; Ohwada, Tomohiko; Shudo, Koichi Journal of Organic Chemistry, 1999 , vol. 64, # 2 p. 611 - 617

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Citation Number: 80

Abstract

The Pictet-Spengler reaction, an acid-catalyzed intramolecular cyclization of intermediate imines of 2-arylethylamine to give 1, 2, 3, 4-tetrahydroisoquinolines, has long been limited to active substrates which bear strongly electron-donating groups such as a methoxy or a hydroxy group on the cyclizing benzene ring. In this paper, we present superacid-catalyzed Pictet-Spengler reactions of imines of 2-phenethylamine, including the prototype Pictet- ...