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Au-Catalyzed Cyclization of Monoallylic Diols

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journal contribution
posted on 21.02.2008, 00:00 by Aaron Aponick, Chuan-Ying Li, Berenger Biannic
The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as −78 °C with catalyst loadings as low as 0.1 mol % to provide the products in 79−99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.