ArticleACS catalysis2022
Copper-Catalyzed Enantioselective Oxysulfenylation of Alkenols: Synthesis of Arylthiomethyl-Substituted Cyclic Ethers.
Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed.
- Potassium thiocyanate-promoted four-component alkoxysulfenylation of styrenes with imidazo[1,2-RSC advances · 2026Article
- Pleiotropic prodrugs for both symptomatic and disease-modifying treatment of Alzheimer's disease.Acta pharmaceutica Sinica. B · 2025Article
- Copper-Catalyzed Cyclization and Alkene Transposition Cascade Enables a Modular Synthesis of Complex Spirocyclic Ethers.Journal of the American Chemical Society · 2025Article
- Radical Cyclization-Initiated Difunctionalization Reactions of Alkenes and Alkynes.Molecules (Basel, Switzerland) · 2024Review
- Copper-catalyzed generation of nitrogen-centered radicals and reactions thereof.ARKIVOC : free online journal of organic chemistry · 2024Article
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Abstract
Saturated heterocycles containing oxygen and sulfur are found in biologically significant molecules. The enantioselective oxysulfenylation of alkenols provides a straightforward synthesis route. To date, organocatalytic methods have dominated this approach. Herein, a complementary approach via copper catalysis is presented. This exoselective method provides enantioenriched arylthiomethyl-substituted tetrahydrofurans, phthalans, isochromans, and morpholines from acyclic alkenols. This method provides the largest scope to date for the exocyclization mode, and with generally high enantioselectivity. The enantioselectivity of this copper-catalyzed oxysulfenylation is rationalized by a proposed mechanism involving alkene oxycupration followed by C─S bond formation via radical-mediated atom transfer.
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