Gold Catalyzed Carbocyclization of Dienyl Acetates to Construct Mutifunctionalized 3-Vinyl Cyclohexanol Derivatives

A convenient new method was developed to construct six-membered 3-vinylcyclohexanols (and piperidine products) and 6-oxabicyclo[3.2.1]octan-7-one derivatives with high diastereoselectivities from 1,6-dienyl acetates via gold catalysis. The reaction proceeded through the nucleophilic addition of the alkenes onto the allylic cation group via a 6-endo-trig process. The substrate’s structure affected the configuration orientation of the allylic cation group in a boatlike transition state, which afforded either the trans-cyclohexanols or cis-piperidine derivatives.