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  • Title: Gold(I)-catalysed cycloisomerisation of 1,6-cyclopropene-enes.
    Author: Miege F, Meyer C, Cossy J.
    Journal: Chemistry; 2012 Jun 18; 18(25):7810-22. PubMed ID: 22588697.
    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.
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