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One-Pot Regio- and Diastereoselective Gold-Catalyzed Propargylation of in Situ Activated Chromones and Consecutive
Julio Álvarez-Valle1, Sergio Fernández1, Cecilia Merino-Robledillo2
1Departamento de Química Orgánica e Inorgánica e Instituto Universitario de Química Organometálica "Enrique Moles", Unidad Asociada al C.S.I.C., Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo, Spain.
Abstract:
Herein, we report a gold-catalyzed propargylation of chromone derivatives by propargylsilanes. Chromones are synergistically activated by the silylium cation resulting from the gold activation of the propargylsilane. The reaction exclusively occurs at the C2-position of the chromone, and a single diastereoisomer is formed. Computational studies performed on the reaction mechanism rationalize the formation of the preferred diastereoisomer. Finally, a dual consecutive cascade reaction based on different gold catalysts enables the formation of complex tricyclic compounds.
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