ArticleNature chemistry2025
Asymmetric dearomative single-atom skeletal editing of indoles and pyrroles.
Article in Nature chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
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- Oxidative Arene Ring-Opening of Benzylic Alcohols.JACS Au · 2026Article
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- Programming Insulator-to-Metallic Transport in Insulating Materials via Surface Single-Atom Engineering.Advanced materials (Deerfield Beach, Fla.) · 2026Article
- From alkynes to spiroindole δ-lactamsChemical science · 2026Article
- Article
- A difluorocarbene-triggered annulation/ring expansion cascadeChemical science · 2026Article
- Asymmetric Catalysis: Recent Advances toward a More Sustainable Synthesis.ACS central science · 2026Review
- A Rh(II) Catalyzed Atropisomer Selective Ring Expansion of 3-Aryl Indoles to 4-Aryl Quinolines.ACS catalysis · 2026Article
- Study on the structural characteristics of nitrogen-containing compounds in co-pyrolysis tar of low rank coal usingScientific reports · 2026Article
- Photoinduced polarity-mismatched transformations of isoquinolines into naphthalenes.Nature communications · 2026Article
- Enantioselective dearomative single-atom skeletal editing of benzofurans.Nature communications · 2025Article
- Chiral hypervalent iodine catalyzed stereoselective skeletal editing of pyrimidine fused heterocycles.Nature communications · 2025Article
- Skeletal editing of pyridines to aryldialdehydes.Nature communications · 2025Article
- Skeletal editing of 4-arylpyrimidines into diverse nitrogen heteroaromatics via four-atom synthons.Nature communications · 2025Article
- Rh-Catalyzed Atroposelective Single-Carbon Insertion.Journal of the American Chemical Society · 2025Article
- Single-carbon-atom transfer toChemical science · 2025Article
- Impact of Induced Fitting and Secondary Noncovalent Interactions on Site-Selective and Enantioselective C-H Functionalization of Arylcyclohexanes.Journal of the American Chemical Society · 2025Article
- Switchable skeletal editing of quinolines enabled by cyclizative sequential rearrangements.Nature chemistry · 2025Article
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Authors and funding
10 authors.
Funding
Abstract
Heterocycle skeletal editing has recently emerged as a powerful tactic for achieving heterocycle-to-heterocycle transmutation without the need for multistep de novo heterocycle synthesis. However, the enantioselective skeletal editing of heteroarenes through single-atom logic remains challenging. Here we report the enantiodivergent dearomative skeletal editing of indoles and pyrroles via an asymmetric carbon-atom insertion, using trifluoromethyl N-triftosylhydrazones as carbene precursors. This strategy provides a straightforward methodology to access enantiomerically enriched six-membered N-heterocycles containing a trifluoromethylated quaternary stereocentre from planar N-heteroarenes. The synthetic utility of this enantiodivergent methodology was demonstrated by a broad evaluation of reaction scope, product derivatization and concise syntheses of drug analogues. Mechanistic studies reveal that the excellent asymmetric induction arises from the initial cyclopropanation step. The asymmetric single-atom insertion strategy is expected to have a broad impact on the field of single-atom skeletal editing and catalytic asymmetric dearomatization of aromatic compounds.
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39609530What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.