ArticleAngewandte Chemie (International ed. in English)2024
Enantioselective S-Alkylation of Sulfenamides by Phase-Transfer Catalysis.
Article in Angewandte Chemie (International ed. in English), 2024. 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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13 citing papers in PubMed.
- A General Platform for S-Stereogenic α-Fluoroalkyl S(IV/VI) Compounds via Enantioselective Radical Fluoroalkylation of Sulfenamides.Angewandte Chemie (International ed. in English) · 2026Article
- Iron-Catalyzed Asymmetric NHAngewandte Chemie (International ed. in English) · 2026Article
- Asymmetric Synthesis ofJournal of the American Chemical Society · 2026Article
- Biocatalytic Enantioselective Oxidation ofOrganic letters · 2026Article
- Circumventing Mukaiyama oxidation: selective S-O bond formation via sulfenamide-alcohol coupling.Beilstein journal of organic chemistry · 2026Article
- Peptide-Catalyzed Asymmetric Amination of Sulfenamides Enabled by DFT-Guided Catalyst Optimization.Journal of the American Chemical Society · 2025Article
- Studies on the Mechanism of Styrene Elimination from Sulfilimines: Hammett and Kinetic Isotope Effect Analysis and Computation.The Journal of organic chemistry · 2025Article
- Asymmetric catalytic reductive transformation of S(VI) to S(IV) for modular access to S(IV)-stereogenic sulfilimine derivatives.Science advances · 2025Article
- Catalytic synthesis of chiral sulfinimidate esters via oxidative esterification of sulfenamides.Nature communications · 2025Article
- Chemoselective Electrochemical Coupling of Thioethers and Primary Amines for Accessing Sulfilimines and Sulfoximines.Journal of the American Chemical Society · 2025Article
- Ruthenium-Catalyzed Enantioselective Alkylation of Sulfenamides: A General Approach for the Synthesis of Drug RelevantJournal of the American Chemical Society · 2025Article
- Assembly of (hetero)aryl sulfilimines via copper-catalyzed enantioselective S-arylation of sulfenamides with (hetero)aryl Iodides.Nature communications · 2025Article
- Sulfilimines from a Medicinal Chemist's Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery.Journal of medicinal chemistry · 2025Article
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3 authors.
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Abstract
A general phase-transfer catalyst (PTC) mediated enantioselective alkylation of N-acylsulfenamides is reported. Essential to achieving high selectivity was the use of the triethylacetyl sulfenamide protecting group along with aqueous KOH as the base under biphasic aqueous conditions to enable the reaction to be performed at -40 °C. With these key parameters, enantiomeric ratios up to 97.5 : 2.5 at the newly generated chiral sulfur center were achieved with an inexpensive cinchona alkaloid derived PTC. Broad scope and excellent functional group compatibility was observed for a variety of S-(hetero)aryl and branched and unbranched S-alkyl sulfenamides. Moreover, to achieve high selectivity for the opposite enantiomer, a pseudoenantiomeric catalyst was designed and synthesized from inexpensive cinchonidine. Given that sulfoximines are a bioactive pharmacophore of ever-increasing interest, selected product sulfilimines were oxidized to the corresponding sulfoximines with subsequent reductive cleavage affording the free-NH sulfoximines in high yields. The utility of the disclosed method was further demonstrated by the efficient asymmetric synthesis of atuveciclib, a phase I clinical candidate for which only chiral HPLC separation had previously been reported for isolation of the desired (R)-sulfoximine stereoisomer.
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