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Synfacts 2011(7): 0748-0748  
DOI: 10.1055/s-0030-1260665
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Axially Chiral 4-Aryl 2-Quinolinones via Intramolecular Hydroarylation of Alkynes

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
T. Shibuya, Y. Shibata, K. Noguchi, K. Tanaka*
Tokyo University of Agriculture and Technology, Japan
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

Fused aromatic compounds can be conveniently prepared via metal-mediated intramolecular hydroarylation of alkenes; however, despite numerous studies of these transformations, enantioselective approaches have not been reported thus far. Using this methodology, the authors reported the palladium-catalyzed enantio­selective synthesis of 4-aryl 2-quinolinones, the compound class which is notable for its pharmaceutical importance. By employing 5 mol% of the palladium catalyst, a range of products was obtained with 44-97% yield and 54-98% ee.