Catalytic Ν-sulfonyliminium ion-mediated cyclizations to α-vinyl-substituted isoquinolines and β-carbolines and applications in metathesis

…, JH VAN MAARSEVEEN, HE SCHOEMAKER…

Index: Kinderman, Sape S.; Wekking, Monique M. T.; Van Maarseveen, Jan H.; Schoemaker, Hans E.; Hiemstra, Henk; Rutjes, Floris P. J. T. Journal of Organic Chemistry, 2005 , vol. 70, # 14 p. 5519 - 5527

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Citation Number: 4

Abstract

Résumé/Abstract Catalytic Sn (OTf) 2-induced cyclization of linear, aryl-containing allylic N, O-acetals produced vinylsubstituted tetrahydroisoquinolines and tetrahydro-1H-β- carbolines. The usefulness of the vinyl moiety in the resulting products was demonstrated via the synthesis of various key building blocks for alkaloid structures. The α-vinyl moiety was utilized in a [2, 3] sigmatropic rearrangement, in ring-closing metathesis and a cross- ...