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Regioselective Cyclizations Utilizing a Gold-Catalyzed [3,3] Propargyl Ester Rearrangement


  • We wish to thank Dr. Virginie Maggiotti for running NOE and decoupling experiments, Dr. Eli Ron and Dr. Phong Vu for useful discussions, and the NSF and the MDS Research Foundation for their financial support.


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Switch-Au-roo: A new strategy for the regioselective synthesis of unsaturated carbocycles by chemoselective activation of a Rauhut–Currier zwitterion surrogate, formed from the Au-catalyzed [3,3] sigmatropic rearrangement of propargylic esters, has been achieved. By reversing the regiochemistry of the propargyl ester the synthesis of either the endo- or exocyclic enones is feasible.