Rhodium-Catalyzed Cross-Aldol Reaction: In Situ Aldehyde-Enolate Formation from Allyloxyboranes and Primary Allylic Alcohols

Authors

  • Luqing Lin,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Kumiko Yamamoto,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. Kanai Life Science Catalysis Project, ERATO Japan Science and Technology Agency, Tokyo 113-0033 (Japan)
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  • Dr. Shigeki Matsunaga,

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. Kanai Life Science Catalysis Project, ERATO Japan Science and Technology Agency, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Prof. Dr. Motomu Kanai

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. Kanai Life Science Catalysis Project, ERATO Japan Science and Technology Agency, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • This work was supported in part by ERATO from JST, a Grant-in-Aid for Scientific Research on Innovative Areas “Molecular Activation Directed toward Straightforward Synthesis” from MEXT, and Naito Foundation. L.L. thanks the Uehara Memorial Foundation for scholarship.

Abstract

original image

Katalytischer Dip: Ein Rh/dippf-Katalysator überführt bei Umgebungstemperatur Aldehyde in Enolborane durch Isomerisierung von Allyloxy- und Homoallyloxyboranen. Eine Ein-Topf-Sequenz aus Isomerisierung und gekreuzter Aldolreaktion liefert die Addukte in guter Ausbeute mit syn-Selektivität. Auch primäre Allyl- und Homoallylalkohole konnten direkt eingesetzt werden.

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