Gold-Catalyzed Oxidative Cyclizations on 1,4-Enynes: Evidence for a γ-Substituent Effect on Wagner–Meerwein Rearrangements


  • We thank National Science Council, Taiwan, for financial support of this work.


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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.