ArticleJournal of the American Chemical Society2024
Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 40 citations in OpenAlex.
- Zr-Mediated Cyclization of Alkynes as a Transferable Protocol for ConstructingACS organic & inorganic Au · 2026Article
- 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
- Regio- and Enantioselective Alkoxycarbonylation of Unactivated Terminal Alkenes under Palladium-Bromide-Monophosphine Catalysis.Journal of the American Chemical Society · 2026Article
- Adapting Bower's intramolecular aziridination reaction allows for a metal-free synthesis of N-H aziridines.Organic & biomolecular chemistry · 2026Article
- Enantioselective Olefin 1,2-Arylamination Catalyzed by a Planar Chiral Indenyl-Rhodium(III) Complex.ACS catalysis · 2026Article
- 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
- Enantioselective 3,4-Oxyamination of 1,3-Dienes Enabled by an Electron-Rich Planar Chiral Rhodium Indenyl Catalyst.Organic letters · 2025Article
- 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
- Stereocontrolled Synthesis of Chiral Helicene-Indenido ansa- and Half-Sandwich Metal Complexes and Their Use in Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Enantiospecific Synthesis of Planar Chiral Rhodium and Iridium Cyclopentadienyl Complexes: Enabling Streamlined and Computer-Guided Access to Highly Selective Catalysts for Asymmetric C-H Functionalizations.Journal of the American Chemical Society · 2024Article
- Rhodium-catalyzed atropodivergent hydroamination of alkynes by leveraging two potential enantiodetermining steps.Science advances · 2024Article
- Article
- 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
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Chiral aziridines are important structural motifs found in natural products and various target molecules. They serve as versatile building blocks for the synthesis of chiral amines. While advances in catalyst design have enabled robust methods for enantioselective aziridination of activated olefins, simple and abundant alkyl-substituted olefins pose a significant challenge. In this work, we introduce a novel approach utilizing a planar chiral rhodium indenyl catalyst to facilitate the enantioselective aziridination of unactivated alkenes. This transformation exhibits a remarkable degree of functional group tolerance and displays excellent chemoselectivity favoring unactivated alkenes over their activated counterparts, delivering a wide range of enantioenriched high-value chiral aziridines. Computational studies unveil a stepwise aziridination mechanism in which alkene migratory insertion plays a central role. This process results in the formation of a strained four-membered metallacycle and serves as both the enantio- and rate-determining steps in the overall reaction.
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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.