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Keywords:

  • carbocycles;
  • gold;
  • rearrangement;
  • regioselectivity;
  • synthetic methods
Thumbnail image of graphical abstract

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.