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Stereoselective synthesis of tetra- and tri-substituted alkenyl nitriles via aminative ring-opening of cyclopropenes with iron-aminyl radical

Author

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  • Qian Wang

    (Nankai University)

  • Jin-Kai Cheng

    (Nankai University
    University of California)

  • Shi-Xiong Tang

    (Nankai University)

  • Kendall N. Houk

    (University of California)

  • Fei Wang

    (Nankai University)

Abstract

The ring opening of cyclopropenes provides a compelling platform for the rapid synthesis of various polysubstituted acyclic alkenes. However, radical-mediated reactions of this type remain underexplored, and none of the existing methods have successfully produced tetrasubstituted olefins with high stereoselectivity. We present here an aminative ring-opening of cyclopropenes with iron-aminyl radical to afford tetrasubstituted alkenyl nitriles in a highly stereoselective manner. Computational studies indicate that both the substrate-directed radical addition and the following stereospecific ring-opening of cyclopropyl radical contribute to the extraordinary stereocontrol observed in the reaction. In addition, trisubstituted alkenyl nitriles could also be obtained using this method or via a base-promoted isomerization of the tetrasubstituted alkenyl nitriles, both with consistently high stereoselectivity.

Suggested Citation

  • Qian Wang & Jin-Kai Cheng & Shi-Xiong Tang & Kendall N. Houk & Fei Wang, 2025. "Stereoselective synthesis of tetra- and tri-substituted alkenyl nitriles via aminative ring-opening of cyclopropenes with iron-aminyl radical," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-58555-2
    DOI: 10.1038/s41467-025-58555-2
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