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Ruthenium-Triggered Ring Opening of Ethynylcyclopropanes: [3+2] Cycloaddition with Aldehydes and Aldimines Involving Metal Allenylidene Intermediates

Authors

  • Dr. Yoshihiro Miyake,

    1. Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan)
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  • Satoshi Endo,

    1. Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan)
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  • Dr. Taichi Moriyama,

    1. Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan)
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  • Prof. Dr. Ken Sakata,

    Corresponding author
    1. Faculty of Pharmaceutical Sciences, Hoshi University, Ebara, Shinagawa-ku, Tokyo 142-8501 (Japan)
    • Faculty of Pharmaceutical Sciences, Hoshi University, Ebara, Shinagawa-ku, Tokyo 142-8501 (Japan)
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  • Prof. Dr. Yoshiaki Nishibayashi

    Corresponding author
    1. Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan)
    • Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan)
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  • This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalyst” from the MEXT (Japan).

Abstract

original image

It's complex: Ruthenium-catalyzed [3+2] cycloaddition of ethynylcyclopropanes with aldehydes and aldimines has been found to give the corresponding 2-ethynyltetrahydrofurans or -pyrrolidines in high to excellent yields. In both cases, the formation of a ruthenium allenylidene complex as a key reactive intermediate is supported by density functional theory calculations. Cp*=η5-C5Me5.

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