- Journal
- CHEMISTRY-A EUROPEAN JOURNAL
- Année
- 2012
- Volume
- 18
- Numéro
- 25
- Pages
- 7810-7822
- Mois
- JUN
- DOI
- 10.1002/chem.201200566
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 a-diazoketones.