title: Gold(I)-catalysed cycloisomerisation of 1,6-cyclopropene-enes.
abstract: The gold(I)-catalysed cycloisomerisation of appropriately substituted 1,6-cyclopropene-enes proceeds through regioselective electrophilic ring opening of the three-membered ring to generate an alkenyl gold carbenoid that achieves the intramolecular cyclopropanation of the remote olefin. This strategy allows straightforward, highly efficient and diastereoselective access to a variety of substituted 3-oxa- and 3-azabicyclo[4.1.0]heptanes, as well as to bicyclo[4.1.0]heptan-3-ol derivatives. Since the isopropylidene group in the resulting cycloisomerisation products can be subjected to ozonolysis, 3,3-dimethylcyclopropenes behave as interesting surrogates for α-diazoketones.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS (UMR 7084), 10 rue Vauquelin 75231 Paris Cedex 05, France.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Miege
authors.forename: Christophe
authors.initials: C
authors.lastname: Meyer
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003521:Cyclopropanes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D006536:Heptanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D003521:Cyclopropanes; D006536:Heptanes; D007659:Ketones; D006046:Gold; C021985:cyclopropene