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Synfacts 2009(2): 0174-0174  
DOI: 10.1055/s-0028-1087644
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Tetrahydroquinolines by Asymmetric Hydrogenation

Contributor(s): Mark Lautens, Frédéric Ménard
Z.-W. Li, T.-L. Wang, Y.-M. He, Z.-J. Wang, Q.-H. Fan*, J. Pan, L.-J. Xu*
Institute of Chemistry, Chinese Academy of Sciences and Renmin University of China, Beijing, P. R. of China
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

The catalytic hydrogenation of ­heteroaromatic compounds is challenging as it ­requires highly reactive catalysts to break the ­aromaticity of the substrates. This high reactivity usually translates into having a catalyst that is very sensitive. The authors have found that the air­stable Ir(III) complex previously used by Ohkuma can achieve the asymmetric hydrogenation of quinolines without special precautions to avoid oxygen in the reaction solvent (Org. Lett. 2007, 9, 2565).