Catalytic N-sulfonyliminium ion-mediated cyclizations to alpha-vinyl-substituted isoquinolines and beta-carbolines and applications in metathesis.

@article{Kinderman2005CatalyticNI,
  title={Catalytic N-sulfonyliminium ion-mediated cyclizations to alpha-vinyl-substituted isoquinolines and beta-carbolines and applications in metathesis.},
  author={S. S. Kinderman and Monique M. T. Wekking and J. V. van Maarseveen and H. Schoemaker and H. Hiemstra and F. Rutjes},
  journal={The Journal of organic chemistry},
  year={2005},
  volume={70 14},
  pages={
          5519-27
        }
}
  • S. S. Kinderman, Monique M. T. Wekking, +3 authors F. Rutjes
  • Published 2005
  • Medicine
  • The Journal of organic chemistry
  • [reaction: see text] Catalytic Sn(OTf)2-induced cyclization of linear, aryl-containing allylic N,O-acetals produced vinyl-substituted tetrahydroisoquinolines and tetrahydro-1H-beta-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 alpha-vinyl moiety was utilized in a [2,3] sigmatropic rearrangement, in ring-closing metathesis and a cross-metathesis-based synthesis of vincantril… CONTINUE READING