title: Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes.
abstract: 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.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Ryan J
authors.initials: RJ
authors.lastname: Felix
authors.forename: Osvaldo
authors.initials: O
authors.lastname: Gutierrez
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
authors.forename: Michel R
authors.initials: MR
authors.lastname: Gagné
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D050607:Organogold Compounds / Q000737:chemistry*; D011789:Quantum Theory
chemical_list: D001643:Bridged Bicyclo Compounds; D050607:Organogold Compounds