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Synfacts 2009(10): 1087-1087  
DOI: 10.1055/s-0029-1217900
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Tetrahydroquinolines by Relay Catalysis

Contributor(s): Victor Snieckus, Timothy Hurst
Z.-Y. Han, H. Xiao, X.-H. Chen, L.-Z. Gong*
University of Science and Technology of China, Hefei, P. R. of China
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

The one-pot asymmetric synthesis of tetrahydroquinolines 2 from 2-(2-propynyl)-anilines 1 under relay catalysis is reported. The ­reaction proceeds via an gold-catalyzed hydro­amination to give 3, followed by Brønsted acid catalyzed enantioselective transfer hydrogenation. The reaction is tolerant of a wide range of functionality on the alkyne including aromatic and aliphatic groups. Electron-withdrawing, -rich, and neutral substituents are also tolerated on the aniline ring. Excellent yields and enantioselectivities were observed in all cases.