ArticleJournal of the American Chemical Society2022
Noncovalent Stabilization of Radical Intermediates in the Enantioselective Hydroamination of Alkenes with Sulfonamides.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- From reagents to feedstocks: reprogramming heteroatom-containing molecules in modern organic synthesis.Molecular diversity · 2026Review
- Overcoming the Barrier to Intermolecular Alkoxy Radical Reactivity: Proton-Coupled Electron Transfer-Mediated Alkene Hydroetherification.Journal of the American Chemical Society · 2026Article
- Best Practices and Considerations for Applying Multiple Linear Regression in Organic Chemistry Research.The Journal of organic chemistry · 2026Review
- Computational study of the mechanism and selectivity of [3 + 2] cycloaddition reactions between nitrone and carbodiimide leading to the formation of anticancer 1,2,4-oxadiazolidine compounds from a MEDT perspective.Scientific reports · 2026Article
- Trisubstituted Alkenes as Valuable Building Blocks.Molecules (Basel, Switzerland) · 2025Review
- Shaping of a Reactive Manganese Catalyst Enables Access to Polyfunctionalized Cyclohexanes via Enantioselective C(spAngewandte Chemie (International ed. in English) · 2025Article
- Interrogation of Enantioselectivity in the Photomediated Ring Contractions of Saturated Heterocycles.Journal of the American Chemical Society · 2025Article
- Article
- The effect of tethered bi-naphthyls on visible-light promoted alkene-alkene [2 + 2] cycloadditions.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2024Article
- Spectrofluorometric investigations on the solvent effects on the photocyclization reaction of diclofenac.Heliyon · 2023Article
- Catalytic Asymmetric Hydrogen Atom Transfer: Enantioselective Hydroamination of Alkenes.Journal of the American Chemical Society · 2023Article
- Radical Hydrocarboxylation of Unactivated Alkenes via Photocatalytic Formate Activation.Journal of the American Chemical Society · 2023Article
- Molecular Understanding and Practical In Silico Catalyst Design in Computational Organocatalysis and Phase Transfer Catalysis-Challenges and Opportunities.Molecules (Basel, Switzerland) · 2023Review
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Authors and funding
6 authors.
Funding
Abstract
Noncovalent interactions (NCIs) are critical elements of molecular recognition in a wide variety of chemical contexts. While NCIs have been studied extensively for closed-shell molecules and ions, very little is understood about the structures and properties of NCIs involving free radical intermediates. In this report, we describe a detailed mechanistic study of the enantioselective radical hydroamination of alkenes with sulfonamides and present evidence suggesting that the basis for asymmetric induction in this process arises from attractive NCIs between a neutral sulfonamidyl radical intermediate and a chiral phosphoric acid (CPA). We describe experimental, computational, and data science-based evidence that identifies the specific radical NCIs that form the basis for the enantioselectivity. Kinetic studies support that C-N bond formation determines the enantioselectivity. Density functional theory investigations revealed the importance of both strong H-bonding between the CPA and the
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