Skip to main content
placeholder image

Synthesis of spirocyclic heterocycles from ¿,ß-unsaturated N -acyliminium ions

Journal Article


Abstract


  • The reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy-5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported. Six single crystal X-ray structures and extensive 2D NMR experiments confirmed the structures and stereochemistries of these products. In addition, computational studies provided mechanistic insights and an understanding of the stereochemical outcomes of these reactions.

Publication Date


  • 2021

Citation


  • Thaima, T., Yazici, A., Auranwiwat, C., Willis, A. C., Wille, U., Limtharakul, T., & Pyne, S. G. (2021). Synthesis of spirocyclic heterocycles from ¿,ß-unsaturated N -acyliminium ions. Organic and Biomolecular Chemistry, 19(1), 259-272. doi:10.1039/d0ob02075c

Scopus Eid


  • 2-s2.0-85099134223

Start Page


  • 259

End Page


  • 272

Volume


  • 19

Issue


  • 1

Abstract


  • The reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy-5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported. Six single crystal X-ray structures and extensive 2D NMR experiments confirmed the structures and stereochemistries of these products. In addition, computational studies provided mechanistic insights and an understanding of the stereochemical outcomes of these reactions.

Publication Date


  • 2021

Citation


  • Thaima, T., Yazici, A., Auranwiwat, C., Willis, A. C., Wille, U., Limtharakul, T., & Pyne, S. G. (2021). Synthesis of spirocyclic heterocycles from ¿,ß-unsaturated N -acyliminium ions. Organic and Biomolecular Chemistry, 19(1), 259-272. doi:10.1039/d0ob02075c

Scopus Eid


  • 2-s2.0-85099134223

Start Page


  • 259

End Page


  • 272

Volume


  • 19

Issue


  • 1