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Au/Ag-catalyzed intramolecular ring-opening of vinylidene-cyclopropanes (VDCPs): an easy access to functional tetrahydropyrans. 2010
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China.
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 [(Ph(3)PAu)(3)O]BF(4) (4 mol %) and AgOTf (4 mol %) was found to catalyze the reaction to completion within 10-30 min in 1,4-dioxane at 60 degrees C to give allene-functionalized tetrahydropyrans.
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