Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes. Academic Article uri icon


  • Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,5-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transformation.

published proceedings

  • J Org Chem

author list (cited authors)

  • Felix, R. J., Gutierrez, O., Tantillo, D. J., & Gagn, M. R.

citation count

  • 22

complete list of authors

  • Felix, Ryan J||Gutierrez, Osvaldo||Tantillo, Dean J||Gagné, Michel R

publication date

  • January 2013