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Synfacts 2006(2): 0141-0141  
DOI: 10.1055/s-2005-924817
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed 1,4-Addition of Arylzinc Reagents

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
R. Shintani, T. Yamagami, T. Kimura, T. Hayashi*
Kyoto University, Japan
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

The authors report on the synthesis of 2-aryl-2,3-dihydro-4-quinolines, a class of important antimitotic antitumor agents, for which the number of effective preparative methods is quite limited so far. High enantioselectivities (in most cases >95% ee) are obtained for a broad scope of substituted 2,3-dihydro-4-quinolone substrates as well as various aryl nucleophiles. TMSCl was found to increase the yield of the reaction, providing silyl enol ethers that gave the corresponding ketone after hydrolytic workup.