Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization - how strain associated with bridging affects 5-exo vs. 6-endo selectivity. Academic Article uri icon

abstract

  • Quantum chemical calculations are used to explore the origins of regioselectivity for proton-, Pt(II)- and Pd(II)-promoted cyclizations of 1,5-hexadienes, 5-aminoalkenes, and allylic acetimidates. The strain associated with achieving carbonium ion-like transition state geometries is shown to be a key factor in controlling 5-exo vs. 6-endo selectivity.

published proceedings

  • Chem Sci

author list (cited authors)

  • Gutierrez, O., Harrison, J. G., Felix, R. J., Guzman, F. C., Gagn, M. R., & Tantillo, D. J.

citation count

  • 8

complete list of authors

  • Gutierrez, Osvaldo||Harrison, Jason G||Felix, Ryan J||Guzman, Fernando Cortés||Gagné, Michel R||Tantillo, Dean J

publication date

  • October 2013