Ruthenium-catalyzed formal [4 + 2] cycloaddition of alkynes with alkenes: formation of cyclohexenedicarboxylates via isomerization of alkynes and successive Diels-Alder reaction |
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| Authors: | Masashi Shiotsuki Takashi Ito Teruyuki Kondo |
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| Institution: | a Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
b Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan |
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| Abstract: | Formal 4 + 2] cycloaddition of alkynes with electron-deficient alkenes, which affords 3,6-dialkyl-4-cyclohexene-1,2-dicarboxylates, was achieved using Ru(η6-1,3,5-cyclooctatriene)(η2-dimethyl fumarate)2 as a catalyst. The reaction mechanism consists of two steps, isomerization of an alkyne to conjugated dienes and successive Diels-Alder reaction of the generated dienes with an electron-deficient alkene. |
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| Keywords: | Ruthenium [4 + 2] Cycloaddition Cyclohexenedicarboxylates Isomerization Diels-Alder reaction |
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