ArticleNature chemistry2024
Asymmetric synthesis of sulfoximines, sulfonimidoyl fluorides and sulfonimidamides enabled by an enantiopure bifunctional S(VI) reagent.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed, 81 citations in OpenAlex.
- Simultaneous Construction of Sulfur and Carbon Stereocenters via Asymmetric Desymmetrization of Sulfonimidamides With Oxindole Derivatives.Angewandte Chemie (International ed. in English) · 2026Article
- N-Alkoxysulfurdiimide Reagents for the One-Step Modular Synthesis of Primary Sulfonimidamides.Angewandte Chemie (International ed. in English) · 2026Article
- Iron-Catalyzed Asymmetric NHAngewandte Chemie (International ed. in English) · 2026Article
- Counteranion-mediated dynamic kinetic asymmetric fluorination to access sulfur-stereogenic center.Nature communications · 2026Article
- Closing the Carbon Loop: Continuous-Flow Synthesis of N-Aroyl Sulfoximines via Electrochemical COChemSusChem · 2026Article
- The palladium-catalysed modular annulative synthesis of cyclic sulfonimidamides.Chemical science · 2026Article
- Enzyme-inspired single-molecule photocatalyst enables singlet-oxygen-driven asymmetric epoxidation and sulfoximination.Nature communications · 2026Article
- Mild Transsulfinamidation Enables Rapid Access to Sulfinamides, Sulfonamides, and Sulfonimidamides.Organic letters · 2026Article
- Regioselective synthesis of aza-saccharinsChemical science · 2026Article
- High-Fidelity Transfer of Chiral Sulfonimidoyl Radicals.Journal of the American Chemical Society · 2026Article
- Asymmetric Synthesis ofJournal of the American Chemical Society · 2026Article
- Catalytic asymmetric sulfonimidoyl transfer to access chiral sulfonimidoyl fluorides and related derivatives.Nature chemistry · 2026Article
- Enantioconvergent Access to Chiral S(VI) Stereocenters by Kinetic Resolution of Sulfonimidoyl Chlorides.Angewandte Chemie (International ed. in English) · 2026Article
- Biocatalytic Enantioselective Oxidation ofOrganic letters · 2026Article
- Asymmetric synthesis of stereogenic-at-sulfur compounds via biocatalytic oxidation with Unspecific Peroxygenases.Nature communications · 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
- Copper-Catalyzed Asymmetric Cyclizative Sulfinamidation: Forging Indole-Based Stereogenic Sulfur(IV) Centers and Atropisomeric Chirality.ACS central science · 2025Article
- Chemoselective Electrochemical Coupling of Thioethers and Primary Amines for Accessing Sulfilimines and Sulfoximines.Journal of the American Chemical Society · 2025Article
- Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides.Nature communications · 2025Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
An increased interest to expand three-dimensional chemical space for the design of new materials and medicines has created a demand for isosteric replacement groups of commonly used molecular functionality. The structural and chemical properties of chiral S(VI) functional groups provide unique spatial and electronic features compared with their achiral sulfur- and carbon-based counterparts. Manipulation of the S(VI) centre to introduce structural variation with stereochemical control has remained a synthetic challenge. The stability of sulfonimidoyl fluorides and the efficiency of sulfur fluorine exchange chemistry has enabled the development of the enantiopure bifunctional S(VI) transfer reagent t-BuSF to overcome current synthetic limitations. Here, we disclose a reagent platform that serves as a chiral sulfur fluorine exchange template for the rapid asymmetric synthesis of over 70 sulfoximines, sulfonimidoyl fluorides and sulfonimidamides with excellent enantiomeric excess and good overall yields. Furthermore, the practical utility of the bifunctional S(VI) transfer reagent was demonstrated in the syntheses of enantiopure pharmaceutical intermediates and analogues.
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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.