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Synfacts 2007(8): 0830-0830  
DOI: 10.1055/s-2007-968763
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Highly Enantioselective Hydrogenation of Quinolines

Contributor(s): Hisashi Yamamoto, Marina Naodovic
D.-W. Wang, W. Zeng, Y.-G. Zhou*
Dalian Institute of Chemical Physics, P. R. of China
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Publikationsdatum:
24. Juli 2007 (online)

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Significance

1,4-Dihydropyridines have been recognized as a potential source of hydrogen when undergoing dehydroaromatization. Such strategy has been exploited here for highly enantio­selective hydrogenation of quinolines. Reduction proceeds smoothly under mild conditions and minimal investment of the catalyst to give a variety of amine products. The reaction is sensitive to the electron-withdrawing substituents in the 6-position which cause decreased reactivity.