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Au/Ag-Catalyzed Intramolecular Ring-Opening of Vinylidene-cyclopropanes (VDCPs): An Easy Access to Functional Tetrahydropyrans

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journal contribution
posted on 05.03.2010, 00:00 by Wei Li, Wei Yuan, Surech Pindi, Min Shi, Guigen Li
An intramolecular ring-opening of vinylidenecyclopropanes (VDCPs) tethered with alcohol chains has been established. A series of transition metal catalysts and their combinations have been screened under mild conditions, and a cocatalyst system consisting of [(Ph3PAu)3O]BF4 (4 mol %) and AgOTf (4 mol %) was found to catalyze the reaction to completion within 10−30 min in 1,4-dioxane at 60 °C to give allene-functionalized tetrahydropyrans.