Iminium ion and acyliminium ion initiated cyclization reactions of vinylsilanes. Regiocontrolled synthesis of tetrahydropyridines and related heterocycles

C Flann, TC Malone, LE Overman

Index: Flann,C.; Malone,T.C.; Overman,L.E. Journal of the American Chemical Society, 1987 ,  vol. 109, p. 6097            

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Citation Number: 72

Abstract

Abstract: 1, 2, 5, 6-Tetrahydropyridines containing substituents at positions 1, 2, 3, and 4 can be prepared in useful yields, with complete regioselectiuity, by the cyclization of iminium ions derived from 4-(trimethylsilyl)-3-butenylamines. The general sequence is illustrated in Scheme I. Three methods for generating the iminium ion intermediate are described. Tetrahydropyridines containing a 1-substituent are most easily prepared by the reaction of ...