ArticleAngewandte Chemie (International ed. in English)2022
Enantioselective Synthesis of Dithia[5]helicenes and their Postsynthetic Functionalization to Access Dithia[9]helicenes.
Article in Angewandte Chemie (International ed. in English), 2022. 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.
- Stereoselective synthesis of E-shaped double helicene analogues via organocatalytic intermolecular cycloaddition.Nature communications · 2026Article
- Enantioselective synthesis of configurationally stable [5]helicenes containing 1,2-azaborine units.Chemical science · 2026Article
- Copper-catalyzed atroposelective hydroarylation of 1-alkynylindoles.Nature communications · 2025Article
- Enantioselective synthesis and racemization dynamics of trithia[5]helicenes derived from the dithieno[2,3-Chemical science · 2025Article
- Catalytic kinetic resolution of helical polycyclic phenols via an organocatalyzed enantioselective dearomative amination reaction.Science advances · 2024Article
- Organocatalytic hydrogen bond donor/Lewis base (HBD/LB) synthesis and chiroptical properties of thiabridged [5]helicenes.Organic & biomolecular chemistry · 2024Article
- Enantioselective synthesis of [4]helicenes by organocatalyzed intermolecular C-H amination.Nature communications · 2024Article
- Electrochemical synthesis of heterodehydro[7]helicenes.Communications chemistry · 2022Article
- Article
- Enantioselective Synthesis of Dithia[5]helicenes and their Postsynthetic Functionalization to Access Dithia[9]helicenes.Angewandte Chemie (International ed. in English) · 2022Article
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7 authors.
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Abstract
A highly enantioselective synthesis of 5,13-disubstituted dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophenes is reported. Key for the successful assembly of these helical architectures is the last two successive Au-catalyzed intramolecular alkyne hydroarylation events. Specifically, the second cyclization is the enantiodetermining step of the whole process and provides the desired helicenes with excellent ee values when a TADDOL-derived 1,2,3-(triazolium)phosphonite moiety (TADDOL: α,α,α',α'-tetraaryl-1,3-dioxolane-4,5-dimethanol) is employed as an ancillary ligand. The absolute stereochemistry of the newly prepared structures has been determined by X-ray crystallography to be P; the optical properties of these heterohelicenes are also reported. A three-step procedure was subsequently developed that allows the transformation of the initially obtained dithia[5]helicenes into dithia[9]helicenes without erosion of the enantiopurity.
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