ArticleJournal of the American Chemical Society2024
Enantioselective Nitrene Transfer to Hydrocinnamyl Alcohols and Allylic Alcohols Enabled by Systematic Exploration of the Structure of Ion-Paired Rhodium Catalysts.
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 7 papers.
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Who cites it
7 citing papers in PubMed.
- 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
- Chiral S(VI) platform unifies selective C-H amination of complex molecules and alkane feedstocks.Science (New York, N.Y.) · 2026Article
- Formal Cyclopropylation of Imines with Cyclopropanols: Stereocontrolled Access to Conformationally Constrained γ-Amino Alcohols.Angewandte Chemie (International ed. in English) · 2025Article
- 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
- 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
Corrections and comments
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Authors and funding
4 authors.
Funding
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Abstract
This work describes highly enantioselective nitrene transfer to hydrocinnamyl alcohols (benzylic C-H amination) and allylic alcohols (aziridination) using ion-paired Rh (II,II) complexes based on anionic variants of Du Bois' esp ligand that are associated with cinchona alkaloid-derived chiral cations. Directed by a substrate hydroxyl group, our previous work with these complexes had not been able to achieve high enantioselectivity on these most useful short-chain compounds, and we overcame this challenge through a combination of catalyst design and modified conditions. A hypothesis that modulation of the linker between the anionic sulfonate group and the central arene spacer might provide a better fit for shorter chain length substrates led to the development of a new biaryl-containing scaffold, which has allowed a broad scope for both substrate classes to be realized for the first time. Furthermore, we describe a systematic structural "knockout" study on the cinchona alkaloid-derived chiral cation to elucidate which features are crucial for high enantioinduction.
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Registered trials
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