ArticleNature communications2025
Stereoselective synthesis of tetra- and tri-substituted alkenyl nitriles via aminative ring-opening of cyclopropenes with iron-aminyl radical.
Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Reaction Pathway and Axial Ligand Effects of C(spJACS Au · 2026Article
- Amine/ammonium buffering enables efficient anti-Markovnikov hydroamination of olefins with alkylamines.Nature communications · 2026Article
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Authors and funding
5 authors.
Funding
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.
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Registered trials
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