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Synlett
DOI: 10.1055/a-2720-9227
Letter

Intramolecular Hydride Shift-Mediated Double C(sp3)–H Bond Functionalization of Conformationally Flexible Aliphatic Alkenylidene Malonates

Authors

  • Sosuke Ando

    1   Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Fuchu, Japan (Ringgold ID: RIN13125)

  • Masahiro Anada

    2   Faculty of Pharmacy, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
    3   Research Institute of Pharmaceutical Sciences, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)

  • Shunsuke Sueki

    2   Faculty of Pharmacy, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
    3   Research Institute of Pharmaceutical Sciences, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)

  • Kosho Makino

    2   Faculty of Pharmacy, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
    3   Research Institute of Pharmaceutical Sciences, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)

  • Tomoko Kawasaki-Takasuka

    4   Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology Faculty of Engineering Graduate School of Engineering, Koganei, Japan (Ringgold ID: RIN98293)
    4   Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology Faculty of Engineering Graduate School of Engineering, Koganei, Japan (Ringgold ID: RIN98293)

  • Keiji Mori 

    1   Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Fuchu, Japan (Ringgold ID: RIN13125)

Supported by: Japan Society for the Promotion of Science
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We report a double C(sp3)-H bond functionalization from a substrate that has no conformational bias, an indispensable factor for achieving the sequential hydride shift process. By employing ZnBr2 as a promoter and low concentration conditions (0.025 M), the sequential hydride shift/cyclization process from an alkenylidene malonate with no substituents on the linker proceeded smoothly, affording dicyclic piperidine derivatives in moderate to good chemical yields with excellent diastereoselectivities.



Publication History

Received: 25 July 2025

Accepted after revision: 10 October 2025

Accepted Manuscript online:
10 October 2025

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