Gold-catalyzed cycloisomerization of [3]-cumulenols

The gold-catalyzed cycloisomerization of tetrasubstituted [3]-cumulenols has been investigated. Overall, two main pathways are followed. In the presence of gold(III) catalysts, a dehydration process prevails giving diastereomerically pure dienynes while gold(I) catalysts favor the cycloisomerization to provide trisubstituted furan derivatives. The gold-catalyzed cycloisomerization of tetrasubstituted [3]-cumulenols has been investigated. Overall, two main pathways are followed. In the presence of gold(III) catalysts, a dehydration process prevails giving diastereomerically pure dienynes while gold(I) catalysts favor the cycloisomerization to provide trisubstituted furan derivatives. [Display omitted] •First gold-catalyzed cycloisomerization of cumulenols.•Reaction outcome dependent from the gold oxidation state.•A new access to trisubstituted furan derivatives.•Gold(I) π-activation of the cumulene moeity.