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Synthesis and Palladium-Catalyzed Cycloaddition of the Bifunctional Conjunctive Reagent Methyl (<i>Z</i>)-1-Methyl-2-trimethylsilylmethyl-2-butenyl Carbonate
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1992
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Excellent RegioselectivityChemical EngineeringCross-coupling ReactionEngineeringAlkene MetathesisPalladium-catalyzed CycloadditionReady AccessOrganic ChemistryOrganometallic CatalysisCatalysisChemistryTitle CompoundEnantioselective SynthesisBiomolecular Engineering
A simple synthesis of (Z)-2-trimethylsilylmethyl-2-buten-1-ol from 2-butyn-1-ol provides ready access to disubstituted bifunctional conjunctive reagents such as the title compound. Palladium(0) catalysts initiate cycloaddition to electron-deficient olefins to form methylenecyclopentanes with excellent regioselectivity.