ArticleAngewandte Chemie (International ed. in English)2021
Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Enhanced Selectivity of Chalcogen Bonding over Halogen Bonding Catalyzed C-glycosylation Through Differentiated Intermediate Activation.Angewandte Chemie (International ed. in English) · 2026Article
- Asymmetric catalytic reductive transformation of S(VI) to S(IV) for modular access to S(IV)-stereogenic sulfilimine derivatives.Science advances · 2025Article
- Catalytic Amino Group Transfer Reactions Mediated by Photoinduced Nitrene Formation from Rhodium-Hydroxamates.Angewandte Chemie (International ed. in English) · 2025Article
- Assembly of (hetero)aryl sulfilimines via copper-catalyzed enantioselective S-arylation of sulfenamides with (hetero)aryl Iodides.Nature communications · 2025Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Synthesis of chiral sulfilimines by organocatalytic enantioselective sulfur alkylation of sulfenamides.Science advances · 2024Article
- Enantioselective Chan-LamNature catalysis · 2024Article
- Review
- Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols.Nature communications · 2022Article
- Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions.Angewandte Chemie (International ed. in English) · 2021Article
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7 authors.
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Abstract
An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding properties of the heterocyclic lactams. A total of 21 chiral sulfimides were obtained in high yields (44-99 %) and with significant enantiomeric excess (70-99 % ee). The sulfimidation proceeds with high site-selectivity and can also be employed for the kinetic resolution of chiral sulfoxides. Mechanistic evidence suggests the intermediacy of a heteroleptic silver complex, in which the silver atom is bound to one molecule of the chiral ligand and one molecule of an achiral 1,10-phenanthroline. Support for the suggested reaction course was obtained by ESI mass spectrometry, DFT calculations, and a Hammett analysis.
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