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Ni-Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights

Authors

  • Dr. Ryu Yamasaki,

    1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
    2. Present Address: Molecular Engineering Institute (MEI), Kinki University, 11-6 Kayanomori, Iizuka, Fukuoka 820-8555 (Japan)
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  • Dr. Masato Ohashi,

    1. Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7394
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  • Kyotaro Maeda,

    1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Takuya Kitamura,

    1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Minami Nakagawa,

    1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Korehito Kato,

    1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Tetsushi Fujita,

    1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Ryohei Kamura,

    1. Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7394
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  • Kazuto Kinoshita,

    1. Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7394
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  • Dr. Hyuma Masu,

    1. Faculty of Pharmaceutical Science at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193 (Japan)
    2. Present Address: Chemical Analysis Center, Chiba University, 1-33 Yayoi-cho, Inage, Chiba 263-8522 (Japan)
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  • Prof. Dr. Isao Azumaya,

    1. Faculty of Pharmaceutical Science at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193 (Japan)
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  • Prof. Dr. Sensuke Ogoshi,

    Corresponding author
    1. Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7394
    • Sensuke Ogoshi, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7394

      Shinichi Saito, Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631

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  • Prof. Dr. Shinichi Saito

    Corresponding author
    1. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
    • Sensuke Ogoshi, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7394

      Shinichi Saito, Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631

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Abstract

A detailed study of the Ni-catalyzed [4+3+2] cycloaddition reaction between ethyl cyclopropylideneacetate and dienynes has been conducted, resulting in the development of a new method for the synthesis of compounds containing nine-membered rings. We studied the reactivity of various dienynes, together with their substituent and conformational effects. The mechanism of the reaction was probed by examining the stoichiometric reactions of the Ni complexes and dienynes.

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