Regioselective Alkylation of Vinylogous N-Acyliminium Ion, Leading to 6-Alkyl-1, 2, 3, 6-tetrahydropyridines, by Using Electrogenerated Acid (EG acid) as a Catalyst

…, T Inokuchi, S Takagishi, F Akahoshi, K Uneyama

Index: Torii, Sigeru; Inokuchi, Tsutomu; Takagishi, Sadahito; Akahoshi, Fumihiko; Uneyama, Kenji Chemistry Letters, 1987 , p. 639 - 642

Full Text: HTML

Citation Number: 8

Abstract

Alkylation of 6-methoxy-1, 2, 3, 6-tetrahydro-and 4-methoxy-1, 2, 3, 4-tetrahydropyridines with organo-silicon compounds as a carbon nucleophile by using electrogenerated acid as an acid catalyst proceeds regioselectively at the C-6 position via vinylogous acyliminium ion, while sulfenylation and methoxylation occurs at the C-4 position.