ArticleNature communications2019
Enantioselective cyanation via radical-mediated C-C single bond cleavage for synthesis of chiral dinitriles.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters.Nature communications · 2025Article
- Manganese-catalyzed base-free addition of saturated nitriles to unsaturated nitriles by template catalysis.Chemical science · 2024Article
- Metal-Catalyzed Enantioconvergent Transformations.Chemical reviews · 2023Review
- Enantioselective catalytic radical decarbonylative azidation and cyanation of aldehydes.Science advances · 2023Article
- Copper-catalyzed asymmetric C(spNature communications · 2023Article
- Recent Advances in N-O Bond Cleavage of Oximes and Hydroxylamines to Construct N-Heterocycle.Molecules (Basel, Switzerland) · 2023Review
- Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6.Chemical science · 2022Article
- Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.Chemical reviews · 2022Review
- Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis.Chemical reviews · 2022Review
- Deacylation-Aided C─H Alkylative Annulation through C─C Cleavage of Unstrained Ketones.Nature catalysis · 2021Article
- Photocatalytic three-component asymmetric sulfonylation via direct C(spNature communications · 2021Article
- Asymmetric three-component olefin dicarbofunctionalization enabled by photoredox and copper dual catalysis.Nature communications · 2021Article
- Stereoinduction in Metallaphotoredox Catalysis.Angewandte Chemie (International ed. in English) · 2021Review
- Generation of Sulfonylated Tetrazoles through an Iron-Catalyzed Multicomponent Reaction Involving Sulfur Dioxide.iScience · 2020Article
- NKG7 makes a better killer.Nature immunology · 2020Article
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Ring-opening reaction via selective cleavage of C-C bond is known as a powerful strategy for construction of complex molecules. Complementary to the ionic process focusing on mostly small ring systems, radical-mediated C-C bond cleavage offers a solution for further diverse enantioselective functionalization benefited from its mild conditions, whereas such asymmetric transformations are still limited to three-membered rings so far. Herein, we describe radical-mediated ring-opening and enantioselective cyanation of four- and five-membered cycloketone oxime esters to access chiral 1,5- and 1,6-dinitriles. Employment of dual photoredox/copper catalysis is essential for the asymmetric ring-opening cyanation of cyclopentanone oxime esters. Both reactions proceed under mild conditions giving chiral dinitriles in high yields and enantioselectivity with low catalyst loading and broad substrate scope. The products dinitriles can be converted to valuable optically active diamides and diamines. Mechanistic studies indicate that the benzylic radical generated via C-C single bond cleavage is involved in the catalytic cycle.
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