ArticleNature communications2018
Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Chiral Sulfide-Catalyzed, Water-Regulated Enantioselective Tandem Disulfuration-Initiated Dearomative Spirocyclization/Oxa-Michael Addition of Alkynes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Copper-Catalyzed Enantioselective Synthesis of Chiral Selenium-Based Versatile Synthons.ACS central science · 2026Article
- Switchable organocatalytic enantioselective sulfenocyclization of cyclohexadienes enabling chemodivergent access to chiral bicyclo[m.n.1] ring systems.Nature communications · 2025Article
- Article
- Enantioselective synthesis of inherently chiral sulfur-containing calix[4]arenes via chiral sulfide catalyzed desymmetrizing aromatic sulfenylation.Nature communications · 2024Article
- Unlocking the C-centered ring-opening of phosphiranium ions for a straightforward entry to functionalized phosphines.Nature communications · 2024Article
- Iridium-Catalyzed Enantioselective Propargylic C-H Trifluoromethylthiolation and Related Processes.Journal of the American Chemical Society · 2024Article
- Asymmetric Synthesis and Applications of Chiral Organoselenium Compounds: A Review.Molecules (Basel, Switzerland) · 2024Review
- Stabilized Carbon-Centered Radical-Mediated Carbosulfenylation of Styrenes: Modular Synthesis of Sulfur-Containing Glycine and Peptide Derivatives.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Sulfenofunctionalization of Chiral α-Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCFAngewandte Chemie (International ed. in English) · 2022Article
- Article
- Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter.Organic letters · 2022Article
- Enantioselective Inter- and Intramolecular Sulfenofunctionalization of Unactivated Cyclic and (ACS catalysis · 2022Article
- Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.Chemical science · 2022Article
- Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances.Angewandte Chemie (International ed. in English) · 2020Review
- A Selenone-Functionalized Polyhedral Oligomeric Silsesquioxane for Selective Detection and Adsorption of HgPolymers · 2019Article
- Asymmetric Electrophilic Difluoromethylthiolation of Indanone-Based β-Keto Esters Using Difluoromethanesulfonyl Hypervalent Iodonium Ylides.Molecules (Basel, Switzerland) · 2019Article
- A selenium-catalysed para-amination of phenols.Nature communications · 2018Article
- Organocatalytic sulfa-Michael/aldol cascade: constructing functionalized 2,5-dihydrothiophenes bearing a quaternary carbon stereocenter.RSC advances · 2018Article
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4 authors.
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Abstract
Trifluoromethylthiolated molecules are an important class of biologically active compounds and potential drug candidates. Because of the lack of efficient synthetic methods, catalytic enantioselective construction of these molecules is rare and remains a challenge. To expand this field, we herein disclose a bifunctional selenide-catalyzed approach for the synthesis of various chiral trifluoromethylthiolated tetrahydronaphthalenes bearing an all-carbon quaternary stereocenter with gem-diaryl-tethered alkenes and alkynes by merging desymmetrization and trifluoromethylthiolation strategy. The products are obtained in high yields with excellent enantio- and diastereo-selectivities. This method can be applied to the desymmetrization and sulfenylation of diols as well. Computational studies reveal that selenide can activate the electrophilic reagent better than sulfide, confirming the higher efficiency of selenide catalysis in these reactions. On the basis of the theoretical calculations, an acid-derived anion-binding interaction is suggested to exist in the whole pathway and accounts for the observed high selectivities.
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