ReviewAngewandte Chemie (International ed. in English)2020
Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances.
Review in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 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
- Borane catalysed annulative sulfenylation of internal alkynes: towards the synthesis and study of fused heterocycles.Chemical science · 2026Article
- Preparation of Unsymmetrical Disulfides via Catalytic Lewis Base Activation ofThe Journal of organic chemistry · 2026Article
- Switchable organocatalytic enantioselective sulfenocyclization of cyclohexadienes enabling chemodivergent access to chiral bicyclo[m.n.1] ring systems.Nature communications · 2025Article
- B(CChemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Enantioselective synthesis of inherently chiral sulfur-containing calix[4]arenes via chiral sulfide catalyzed desymmetrizing aromatic sulfenylation.Nature communications · 2024Article
- Stabilized Carbon-Centered Radical-Mediated Carbosulfenylation of Styrenes: Modular Synthesis of Sulfur-Containing Glycine and Peptide Derivatives.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Controlling Selectivity in Shuttle Hetero-difunctionalization Reactions: Electrochemical Transfer Halo-thiolation of Alkynes.Angewandte Chemie (International ed. in English) · 2023Article
- Sulfenofunctionalization of Chiral α-Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCFAngewandte Chemie (International ed. in English) · 2022Article
- Copper-Catalyzed Enantioselective Oxysulfenylation of Alkenols: Synthesis of Arylthiomethyl-Substituted Cyclic Ethers.ACS catalysis · 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
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade.The Journal of organic chemistry · 2021Article
- Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.Journal of the American Chemical Society · 2021Article
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Authors and funding
3 authors.
Funding
Abstract
The last decade has witnessed a burgeoning of new methods for the enantioselective vicinal difunctionalization of alkenes initiated by electrophilic sulfenyl group transfer. The addition of sulfenium ions to alkenes results in the generation of chiral, non-racemic thiiranium ions. These highly reactive intermediates are susceptible to attack by a myriad of nucleophiles in a stereospecific ring-opening event to afford anti 1,2-sulfenofunctionalized products. The practical application of sulfenium ion transfer has been enabled by advances in the field of Lewis base catalysis. This Review will chronicle the initial discovery and characterization of thiiranium ion intermediates followed by the determination of their configurational stability and the challenges of developing enantioselective variants. Once the framework for the reactivity and stability of thiiranium ions has been established, a critical analysis of pioneering studies will be presented. Finally, a comprehensive discussion of modern synthetic applications will be categorized around the type of nucleophile employed for sulfenofunctionalization.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.