ArticleNature chemistry2022
Amino-oxetanes as amide isosteres by an alternative defluorosulfonylative coupling of sulfonyl fluorides.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Fluorinated Aminopiperidones as Non-Glutarimide Thalidomide Analogs: Stereodivergent Synthesis and Validation.ChemMedChem · 2026Article
- Iron-Catalyzed Friedel-Crafts Reactions of Unactivated 3-Aryl-Oxetanols Exploiting HFIP Stabilization of Carbocations.The Journal of organic chemistry · 2026Article
- One pot sulfur(IV) fluoride-mediated deoxyaminations for the syntheses of 3,3-arylamino oxetanes and azetidines.Communications chemistry · 2026Article
- Leveraging Lewis acid catalysis for cascade construction of multisubstituted furans from active methylenes and 3-oxetanone.Communications chemistry · 2026Article
- Do Amino-Oxetanes Resemble Amides? A Matched Molecular Pairs Property and Structural Comparison.Journal of medicinal chemistry · 2026Article
- Upcycling carbon fibre wastes in solid-flames.Nature communications · 2026Article
- Alkyl sulfonyl fluorides as ambiphiles in the stereoselective palladium(II)-catalysed cyclopropanation of unactivated alkenes.Nature synthesis · 2026Article
- A Unified Synthetic Approach to 2-Alkyl Azetidines, Oxetanes, Thietanes and Cyclobutanes from Unactivated Alkenes.Journal of the American Chemical Society · 2025Article
- HFIP-assisted Brønsted acid-catalyzed ring opening of 1-azabicyclo[1.1.0]butane to access diverse C3-quaternary aza-azetidines and indole-azetidines.Nature communications · 2025Article
- Synthesis ofThe Journal of organic chemistry · 2025Article
- Biocatalytic enantioselective formation and ring-opening of oxetanes.Nature communications · 2025Article
- Oxetanes: formation, reactivity and total syntheses of natural products.Beilstein journal of organic chemistry · 2025Review
- Harnessing Oxetane and Azetidine Sulfonyl Fluorides for Opportunities in Drug Discovery.Journal of the American Chemical Society · 2024Article
- Synthesis of 3,3-Disubstituted Thietane Dioxides.The Journal of organic chemistry · 2024Article
- Late-stage meta-C-H alkylation of pharmaceuticals to modulate biological properties and expedite molecular optimisation in a single step.Nature communications · 2024Article
- Multicomponent Synthesis of α-Branched Amines via a Zinc-Mediated Carbonyl Alkylative Amination Reaction.Journal of the American Chemical Society · 2024Article
- Applications of oxetanes in drug discovery and medicinal chemistry.European journal of medicinal chemistry · 2023Review
- Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions.The Journal of organic chemistry · 2023Article
- Oxetanes in Drug Discovery Campaigns.Journal of medicinal chemistry · 2023Review
- Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions.Organic letters · 2023Article
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13 authors.
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No grant is acknowledged in the PubMed record.
Abstract
Bioisosteres provide valuable design elements that medicinal chemists can use to adjust the structural and pharmacokinetic characteristics of bioactive compounds towards viable drug candidates. Aryl oxetane amines offer exciting potential as bioisosteres for benzamides-extremely common pharmacophores-but are rarely examined due to the lack of available synthetic methods. Here we describe a class of reactions for sulfonyl fluorides to form amino-oxetanes by an alternative pathway to the established SuFEx (sulfonyl-fluoride exchange) click reactivity. A defluorosulfonylation forms planar oxetane carbocations simply on warming. This disconnection, comparable to a typical amidation, will allow the application of vast existing amine libraries. The reaction is tolerant to a wide range of polar functionalities and is suitable for array formats. Ten oxetane analogues of bioactive benzamides and marketed drugs are prepared. Kinetic and computational studies support the formation of an oxetane carbocation as the rate-determining step, followed by a chemoselective nucleophile coupling step.
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