ArticleACS catalysis2023
Asymmetric Photoaerobic Lactonization and Aza-Wacker Cyclization of Alkenes Enabled by Ternary Selenium-Sulfur Multicatalysis.
Article in ACS catalysis, 2023. 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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Who cites it
5 citing papers in PubMed.
- Selenium-catalyzed organic transformations.iScience · 2026Review
- A planar chiral organoselenium enabled enantioselective intramolecular oxidation of trisubstituted olefins.Nature communications · 2025Article
- Asymmetric Migratory Tsuji-Wacker Oxidation Enables the Enantioselective Synthesis of Hetero- and Isosteric Diarylmethanes.Journal of the American Chemical Society · 2024Article
- Asymmetric Synthesis and Applications of Chiral Organoselenium Compounds: A Review.Molecules (Basel, Switzerland) · 2024Review
- Intermolecular Aza-Wacker Coupling of Alkenes with Azoles by Photo-Aerobic Selenium-π-Acid Multicatalysis.ACS catalysis · 2024Article
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Authors and funding
7 authors.
Funding
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Abstract
An adaptable, sulfur-accelerated photoaerobic selenium-π-acid ternary catalyst system for the enantioselective allylic redox functionalization of simple, nondirecting alkenes is reported. In contrast to related photoredox catalytic methods, which largely depend on olefinic substrates with heteroatomic directing groups to unfold high degrees of stereoinduction, the current protocol relies on chiral, spirocyclic selenium-π-acids that covalently bind to the alkene moiety. The performance of this ternary catalytic method is demonstrated in the asymmetric, photoaerobic lactonization and cycloamination of enoic acids and unsaturated sulfonamides, respectively, leading to an averaged enantiomeric ratio (er) of 92:8. Notably, this protocol provides for the first time an asymmetric, catalytic entryway to pharmaceutically relevant 3-pyrroline motifs, which was used as a platform to access a 3,4-dihydroxyproline derivative in only seven steps with a 92:8 er.
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Registered trials
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