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Synfacts 2008(9): 0954-0954  
DOI: 10.1055/s-2008-1078001
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rh-Catalyzed [2+2+2] Cycloaddition of
1,6-Diynes

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
K. Tanaka*, M. Takahashi, H. Imase, T. Osaka, K. Noguchi, M. Hirano
Tokyo University of Agriculture and Technology, Japan
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

In previous studies, Shibata and others have described asymmetric Rh(I)-catalyzed [2+2+2] cycloadditions of 1,6-diynes with mono­alkenes containing an alkoxycarbonyl functionality (J. Am. Chem. Soc. 2006, 128, 13686). In the present work, the authors utilize a Rh(I)/BINAP complex to effect the cycloaddition of various 1,6-diynes with a protected dehydroamino acid. Strong bidentate coordination through the alkene and amide carbonyl moieties with rhodium should provide a tight chelate, leading to high levels of asymmetric induction.