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Keywords:

  • carbenes;
  • cyclization;
  • gold;
  • homogeneous catalysis;
  • Wagner–Meerwein rearrangement
Thumbnail image of graphical abstract

Gold-catalyzed oxidative cyclizations of 1,4-enynes were used to study the γ-effect on the Wagner–Meerwein rearrangement. Both experimental and theoretical work disclose that a gold substituent in the γ-position can direct a stereospecific 1,2-shift of the anti-β-substituent regardless of its intrinsic properties.