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Ruthenium-Catalyzed Addition of Primary Amides to Alkynes: A Stereoselective Synthesis of Secondary Enamides
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2009
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Asymmetric CatalysisChemical EngineeringCross-coupling ReactionRuthenium-catalyzed AdditionEngineeringNovel OrganocatalystsAnti-markovnikov AdditionOrganic ChemistryCatalysisStereoselective SynthesisChemistryPrimary AmidesStable E-isomersSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringSecondary Enamides
The anti-Markovnikov addition of primary amides to terminal alkynes under the formation of Z-configured secondary enamides is efficiently promoted by a catalyst system generated in situ from bis(2-methallyl)(cycloocta-1,5-diene)ruthenium(II), 1,4-bis(dicyclohexylphosphino)butane, and ytterbium triflate. The thermodynamically more stable E-isomers are accessible by combining the above hydroamidation with an in situ double-bond isomerization reaction, using triethylamine and molecular sieves.