Insights into the Gold-Catalyzed Cycloisomerization of 3-Allyl-1,4-diynes for the Synthesis of Bicyclic Hydrocarbons

Abstract

An efficient protocol for the synthesis of 3-ethynyl-2-aryl-bicyclo[3.1.0]hexenes through a gold-catalyzed enyne cyclization was established in this work. Depending on the specific substitution pattern, unusual cationic rearrangements of the corresponding gold carbene were revealed, leading to either cyclohexadienes or 5,9-methanobenzo[8]annulene derivatives, respectively.