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Synfacts 2008(9): 0940-0940  
DOI: 10.1055/s-2008-1078007
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Double [2+2+2] Cycloaddition

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
G. Nishida, S. Ogaki, Y. Yusa, T. Yokozawa, K. Noguchi, K. Tenaka*
Tokyo University of Agriculture and Technology and Takasago International Corporation, Kanagawa, Japan
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

This paper describes a cationic rhodium(I)/Segphos complex catalyzed double [2+2+2] cycloaddition of internal 1,6-diynes with a phosphonate- or ester-substituted 1,3-butadiyne. C 2-Symmetric axially chiral biaryl diphosphonates or dicarboxylates, respectively, were obtained in high yields and outstanding enantioselectivities. Moreover, the authors demonstrated the practicality of this method in a large-scale reaction which gave the product with almost identical yield and enantioselectivity as those in the small-scale reaction.