Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols

Abstract

Catalytic intramolecular additions of hydroxyl groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60 °C in the presence of 5 mol % of (PPh 3)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetrahydropyrans in good yields. This reaction represents an atom-economic route to construct five- and six-membered cyclic ethers. © 2012 Elsevier Ltd. All rights reserved.