ArticleJournal of the American Chemical Society2023
Substrate-Directed Enantioselective Aziridination of Alkenyl Alcohols Controlled by a Chiral Cation.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 55 citations in OpenAlex.
- Catalytic Enantioselective Aziridination of Z-Disubstituted Alkenes with Aspartyl β-Turn-Based Dirhodium(II) Metallopeptides and Assessment of Catalyst Scaffold Versatility.Journal of the American Chemical Society · 2026Article
- Palladium-catalyzed enantioselective alkenylation of acyclic alkenols: Broad scope with alkenyl bromides.Science advances · 2026Article
- Chiral S(VI) platform unifies selective C-H amination of complex molecules and alkane feedstocks.Science (New York, N.Y.) · 2026Article
- Adapting Bower's intramolecular aziridination reaction allows for a metal-free synthesis of N-H aziridines.Organic & biomolecular chemistry · 2026Article
- Rearrangement of Protected Epoxy-Alcohols into Tetrahydrofuran Derivatives: The Protecting Group Matters!Tetrahedron · 2025Article
- Synthesis and Application of Bioactive N-Functionalized Aziridines.Angewandte Chemie (International ed. in English) · 2025Review
- Recent Developments in Catalytic Asymmetric Aziridination.Topics in current chemistry (Cham) · 2025Review
- Allylic Amination of Alkenyl Alcohols: Simultaneous Control of Chemoselectivity and Enantioselectivity in Nitrene Transfer Using Ion-Paired Catalysts.ACS catalysis · 2025Article
- Future Trends in Asymmetric Organo-Metal Combined Catalysis.ACS central science · 2025Review
- Asymmetric Aziridination of Allylic Carbamates Using Ion-Paired Rhodium Complexes and Extrapolation to C─H Amination of Phenethyl Carbamates.Angewandte Chemie (International ed. in English) · 2025Article
- Design Approaches That Utilize Ionic Interactions to Control Selectivity in Transition Metal Catalysis.Chemical reviews · 2025Review
- Article
- Asymmetric phase-transfer catalysis.Nature reviews. Chemistry · 2024Review
- Enantioselective Nitrene Transfer to Hydrocinnamyl Alcohols and Allylic Alcohols Enabled by Systematic Exploration of the Structure of Ion-Paired Rhodium Catalysts.Journal of the American Chemical Society · 2024Article
- Application of sSPhos as a Chiral Ligand for Palladium-Catalyzed Asymmetric Allylic Alkylation.Organic letters · 2024Article
- Aziridination via Nitrogen-Atom Transfer to Olefins from Photoexcited Azoxy-Triazenes.Journal of the American Chemical Society · 2024Article
- Enantioselective Phase-Transfer-Catalyzed Synthesis of Spirocyclic Azetidine Oxindoles.Organic letters · 2024Article
- Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst.Journal of the American Chemical Society · 2024Article
- Catalytic, asymmetric carbon-nitrogen bond formation using metal nitrenoids: from metal-ligand complexesChemical science · 2023Review
- Interrogating the Crucial Interactions at Play in the Chiral Cation-Directed Enantioselective Borylation of Arenes.ACS catalysis · 2023Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Alkene aziridination is a highly versatile transformation for the construction of chiral nitrogen-containing compounds. Inspired by the success of analogous substrate-directed epoxidations, we report an enantioselective aziridination of alkenyl alcohols, which enables asymmetric nitrene transfer to alkenes with varied substitution patterns, including those not covered by the current protocols. We believe that our method is effective because it is substrate-directed, exploiting a network of attractive non-covalent interactions between the substrate, an achiral dianionic rhodium(II,II) tetracarboxylate dimer, and its two associated cinchona alkaloid-derived cations. It is these cations that provide a defined chiral pocket in which the aziridination can occur. In addition to a thorough evaluation of compatible alkene classes, we advance a practical mnemonic to predict reaction outcome and disclose a range of post-functionalization protocols that highlight the unique synthetic potential of the enantioenriched aziridine-alcohol products.
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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.