Ruthenium-catalyzed allylation–cyclization reactions of cyclic 1,3-dicarbonyl compounds with 1-vinyl propargyl alcohols that lead to diverse carbo- or heterocyclic products in a one-pot cascade process are reported. These mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex that contains a redox-coupled dienone ligand. The reaction pathway strongly depends on the substrate substitution pattern, which determines the mode of activation of the 1-vinyl propargyl alcohol. The environmentally benign process, which generates water as the only waste product, is of wide scope and allows the atom-economic synthesis of highly functionalized furans, pyrans, and spirocarbocycles.
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