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

Qian Wang, Jin-Kai Cheng, Shi-Xiong Tang, Kendall N. Houk () and Fei Wang ()
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Qian Wang: Nankai University
Jin-Kai Cheng: Nankai University
Shi-Xiong Tang: Nankai University
Kendall N. Houk: University of California
Fei Wang: Nankai University

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: 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.

Date: 2025
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DOI: 10.1038/s41467-025-58555-2

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