ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Synthesis of Highly Enantioenriched Sulfonimidoyl Fluorides and Sulfonimidamides by Stereospecific Sulfur-Fluorine Exchange (SuFEx) Reaction.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
44 citing papers in PubMed.
- Control of axial stereochemistry for the enantioselective construction of a QUINAP library.Chemical science · 2026Article
- Unlocking catalytic asymmetric transformations of sulfilimidoyl fluorides toward chiral sulfinimidate esters.Chemical science · 2026Article
- N-Alkoxysulfurdiimide Reagents for the One-Step Modular Synthesis of Primary Sulfonimidamides.Angewandte Chemie (International ed. in English) · 2026Article
- Direct Stereospecific Deoxyamination of Alcohols Enabled by Li-Mediated SuFEx.Organic letters · 2026Article
- Counteranion-mediated dynamic kinetic asymmetric fluorination to access sulfur-stereogenic center.Nature communications · 2026Article
- Regioselective synthesis of aza-saccharinsChemical science · 2026Article
- Catalytic asymmetric sulfonimidoyl transfer to access chiral sulfonimidoyl fluorides and related derivatives.Nature chemistry · 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
- Assessing Fluorosulfonyl Pentafluorooxosulfate (FSOAngewandte Chemie (International ed. in English) · 2025Article
- Electrochemical Conversions of Sulfenamides into Sulfonimidoyl- and Sulfondiimidoyl Fluorides.JACS Au · 2025Article
- Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides.Nature communications · 2025Article
- Photoredox-catalyzed deoxygenative radical transformation of alcohols to sulfinamides.RSC advances · 2025Article
- Synthesis of chiral sulfilimines by organocatalytic enantioselective sulfur alkylation of sulfenamides.Science advances · 2024Article
- Strain-release driven reactivity of a chiral SuFEx reagent provides stereocontrolled access to sulfinamides, sulfonimidamides, and sulfoximines.Nature communications · 2024Article
- Enantioselective sulfur(VI) fluoride exchange reaction of iminosulfur oxydifluorides.Nature chemistry · 2024Article
- Sulfur stereochemistry takes centre stage.Nature chemistry · 2024Article
- Asymmetric synthesis of sulfoximines, sulfonimidoyl fluorides and sulfonimidamides enabled by an enantiopure bifunctional S(VI) reagent.Nature chemistry · 2024Article
- C-SuFEx linkage of sulfonimidoyl fluorides and organotrifluoroborates.Nature communications · 2024Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors.
Funding
Abstract
Sulfonimidamides present exciting opportunities as chiral isosteres of sulfonamides, with potential for additional directional interactions. Here, we present the first modular enantioselective synthesis of sulfonimidamides, including the first stereoselective synthesis of enantioenriched sulfonimidoyl fluorides, and studies on their reactivity. A new route to sulfonimidoyl fluorides is presented from solid bench-stable, N-Boc-sulfinamide (Boc=tert-butyloxycarbonyl) salt building blocks. Enantioenriched arylsulfonimidoyl fluorides are shown to be readily racemised by fluoride ions. Conditions are developed, which trap fluoride and enable the stereospecific reaction of sulfonimidoyl fluorides with primary and secondary amines (100 % es, es=enantiospecificity) generating sulfonimidamides with up to 99 % ee. Aryl and alkyl sulfonimidoyl fluoride reagents are suitable for mild late stage functionalisation reactions, exemplified by coupling with a selection of complex amines in marketed drugs.
Indexed as
Identifiers
What OpenQuestion holds
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.