ArticleThe Journal of organic chemistry2017
Catalytic, Enantioselective, Intramolecular Sulfenofunctionalization of Alkenes with Phenols.
Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Cationic Cascade Strategy for the Synthesis of Dihydrobenzofuran and Isochromane Scaffolds.Organic letters · 2026Article
- Three-Component Catalytic Amino Etherification of Alkenes: Enabled by Silyl Ether-Promoted C-O Coupling.ACS catalysis · 2025Article
- General Modular and Convergent Approach to Diversely Functionalized Allylic Systems.Journal of the American Chemical Society · 2025Article
- Switchable organocatalytic enantioselective sulfenocyclization of cyclohexadienes enabling chemodivergent access to chiral bicyclo[m.n.1] ring systems.Nature communications · 2025Article
- Article
- Review
- Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade.The Journal of organic chemistry · 2021Article
- Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation.The Journal of organic chemistry · 2021Article
- Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances.Angewandte Chemie (International ed. in English) · 2020Review
- Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes.Organic letters · 2020Article
- Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes.Journal of the American Chemical Society · 2019Article
- Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes.Angewandte Chemie (International ed. in English) · 2019Article
- (Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2019Article
- Unusual Kinetic Profiles for Lewis Base-Catalyzed Sulfenocyclization ofSynlett : accounts and rapid communications in synthetic organic chemistry · 2019Article
- Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes.Journal of the American Chemical Society · 2018Article
- Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.Journal of the American Chemical Society · 2018Article
- Structural, Mechanistic, Spectroscopic, and Preparative Studies on the Lewis Base Catalyzed, Enantioselective Sulfenofunctionalization of Alkenes.Helvetica chimica acta · 2017Article
- Synthesis of 2-Alkenyl-Tethered Anilines.Synthesis · 2017Article
- Electrophilic Selenium Catalysis with Electrophilic N-F Reagents as the Oxidants.Molecules (Basel, Switzerland) · 2017Review
- Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines.The Journal of organic chemistry · 2017Article
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Authors and funding
2 authors.
Funding
Abstract
The catalytic, enantioselective, cyclization of phenols with electrophilic sulfenophthalimides onto isolated or conjugated alkenes affords 2,3-disubstituted benzopyrans and benzoxepins. The reaction is catalyzed by a BINAM-based phosphoramide Lewis base catalyst which assists in the highly enantioselective formation of a thiiranium ion intermediate. The influence of nucleophile electron density, alkene substitution pattern, tether length and Lewis base functional groups on the rate, enantio- and site-selectivity for the cyclization is investigated. The reaction is not affected by the presence of substituents on the phenol ring. In contrast, substitutions around the alkene strongly affect the reaction outcome. Sequential lengthening of the tether results in decreased reactivity, which necessitated increased temperatures for reaction to occur. Sterically bulky aryl groups on the sulfenyl moiety prevented erosion of enantiomeric composition at these elevated temperatures. Alcohols and carboxylic acids preferentially captured thiiranium ions in competition with phenolic hydroxyl groups. An improved method for the selective C(2) allylation of phenols is also described.
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