Gold-catalyzed cycloisomerization of [3]-cumulenols

• 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.

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.Figure optionsDownload as PowerPoint slide