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Synfacts 2010(1): 0059-0059  
DOI: 10.1055/s-0029-1218514
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Ir-Catalyzed Asymmetric Hydrogenation of 2-Aryl- and 2-Alkylquinolinium Salts

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
H. Tadaoka, D. Cartigny, T. Nagano, T. Gosavi, T. Ayad, J.-P. Genêt, T. Ohshima*, V. Ratovelomanana-Vidal*, K. Mashima*
Osaka University, Japan and École Nationale Supérieure de Chimie de Paris, France
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

The 2-substituted 1,2,3,4-tetrahydroquinoline moiety can be found in a number of important biologically active molecules. Despite the development of efficient asymmetric hydrogenation of 2-alkylquinolines, only limited success has been achieved for 2-aryl analogues. In this ­paper, the authors describe the first highly enan­tioselective protocol for hydrogenation of 2-aryl-quinolinium salts using a dinuclear-bridged iridium(III) complex with (S)-difluorphos as a chiral phosphine. A number of 2-arylquinolines were converted into the corresponding products with high yields and good to excellent enantioselectivities (62-95% ee). Notably, 2-alkyl-substituted substrates also showed excellent stereochemical outcome.