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Ruthenium-Catalyzed Addition of Primary Amides to Alkynes: A Stereoselective Synthesis of Secondary Enamides

Lukas J. Gooßen*, Mathieu Blanchot, Kifah S. M. Salih, Käthe Gooßen

*Fachbereich Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße 54, 67663 Kaiserslautern, Germany, Email:

L. J. Gooßen, M. Blanchot, F. S. M. Salih, K. Gooßen, Synthesis, 2009, 2283-288.

DOI: 10.1055/s-0029-1216847

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A catalyst system generated in situ from bis(2-methallyl)(cycloocta-1,5-diene)ruthenium(II), 1,4-bis(dicyclohexylphosphino)butane, and ytterbium triflate promotes an anti-Markovnikov addition of primary amides to terminal alkynes under the formation of Z-configured secondary enamides. An in situ double-bond isomerization reaction using triethylamine and molecular sieves provides E-isomers.

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Ru-Catalyzed Anti-Markovnikov Addition of Amides to Alkynes: A Regio- and Stereoselective Synthesis of Enamides

L. J. Goossen, J. E. Rauhaus, G. Deng, Angew. Chem. Int. Ed., 2005, 44, 4042-4045.

Key Words

alkynes, amides, enamides, hydroamidation, ruthenium

ID: J66-Y2009-2000