ArticleJournal of the American Chemical Society2024
Enantioselective Sulfonimidamide Acylation via a Cinchona Alkaloid-Catalyzed Desymmetrization: Scope, Data Science, and Mechanistic Investigation.
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 12 papers.
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Who cites it
12 citing papers in PubMed.
- Simultaneous Construction of Sulfur and Carbon Stereocenters via Asymmetric Desymmetrization of Sulfonimidamides With Oxindole Derivatives.Angewandte Chemie (International ed. in English) · 2026Article
- Assessment of Complementary Catalysts in an Uncharted Enantioselective Reaction of Sulfondiimines.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
- Understanding and Enhancing Stereoselective Polymerization Using a Data Science Approach.Journal of the American Chemical Society · 2025Article
- Palladium-catalyzed enantioselective dienylation of propargylic carbonates via sulfonimidamide desymmetrization.Nature communications · 2025Article
- Peptide-Catalyzed Asymmetric Amination of Sulfenamides Enabled by DFT-Guided Catalyst Optimization.Journal of the American Chemical Society · 2025Article
- Data-Driven Prediction of Enantioselectivity for the Sharpless Asymmetric Dihydroxylation: Model Development and Experimental Validation.ACS central science · 2025Article
- Chemoselective Electrochemical Coupling of Thioethers and Primary Amines for Accessing Sulfilimines and Sulfoximines.Journal of the American Chemical Society · 2025Article
- Stereodivergent Synthesis of ComplexOrganic letters · 2025Article
- Applying statistical modeling strategies to sparse datasets in synthetic chemistry.Science advances · 2025Review
- Carbene-catalyzed chirality-controlled site-selective acylation of saccharides.Nature communications · 2025Article
- Synthesis of chiral sulfilimines by organocatalytic enantioselective sulfur alkylation of sulfenamides.Science advances · 2024Article
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Authors and funding
12 authors.
Funding
Abstract
Methods to access chiral sulfur(VI) pharmacophores are of interest in medicinal and synthetic chemistry. We report the desymmetrization of unprotected sulfonimidamides via asymmetric acylation with a cinchona-phosphinate catalyst. The desired products are formed in excellent yield and enantioselectivity with no observed bis-acylation. A data-science-driven approach to substrate scope evaluation was coupled to high throughput experimentation (HTE) to facilitate statistical modeling in order to inform mechanistic studies. Reaction kinetics, catalyst structural studies, and density functional theory (DFT) transition state analysis elucidated the turnover-limiting step to be the collapse of the tetrahedral intermediate and provided key insights into the catalyst-substrate structure-activity relationships responsible for the origin of the enantioselectivity. This study offers a reliable method for accessing enantioenriched sulfonimidamides to propel their application as pharmacophores and serves as an example of the mechanistic insight that can be gleaned from integrating data science and traditional physical organic techniques.
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