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

Lukas J. Gooßen*, Jan E. Rauhaus, Guojun Deng

*Institut für Chemie - Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Straße, Geb. 54, 67663 Kaiserslautern Email: goossenchemie.uni-kl.de

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

DOI: 10.1002/anie.200462844

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Abstract

A mild, ruthenium-catalyzed anti-Markovnikov addition of secondary amides, anilides, lactames, ureas, bislactames, and carbamates to terminal alkynes has been developped. Two complementary protocols provide either the E or the Z isomers.

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

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

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Key Words

alkynes, amides, carbamates, ureas, enamides, homogeneous catalysis, hydroamidation, ruthenium

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ID: J06-Y2005-510