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Ryan C. Conyers and Prof. Dr. Benjamin W. Gung Gold(I)-Catalyzed Divergence in the Preparation of Bicyclic Enol Esters: From Exclusively [3C+2C]-Cycloaddition Reactions to Exclusive Formation of Vinylcyclopropanes Chemistry - A European Journal 19

Article first published online: 13 NOV 2012 | DOI: 10.1002/chem.201202881

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Sense and sensitivity: The outcome of the AuI-catalyzed reactions of propargyl esters with cyclic vinyl ethers is sensitive to substrate structure (see scheme). The preference for the [3C+2C] cycloaddition pathway may depend on the degree of polarization of the vinyl ether double bond. A more polarized π-bond appears to induce [3C+2C] cycloaddition whereas a less polarized π-bond preferentially undergoes cyclopropanation reactions.

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