ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light-Mediated Cycloadditions.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Bifunctional Photocatalysts: Exploiting Proximity for Enhanced Reaction Performance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Role of 2-Hydroxyimines in Chiral Phosphoric Acid-Catalyzed Mannich-Type Reactions: Enhancing Reactivity and Selectivity via Dimerization.Journal of the American Chemical Society · 2026Article
- Photochemical deracemization of 2,3-allenoic acids mediated by a sensitizing chiral phosphoric acid catalyst.Chemical science · 2025Article
- Enantioselective Photochemical Generation of a Short-Lived, Twisted Cycloheptenone Isomer: Catalytic Formation, Detection, and Consecutive Chemistry.Angewandte Chemie (International ed. in English) · 2025Article
- Asymmetric photoreactions catalyzed by chiral ketones.RSC advances · 2025Review
- Hybrid Catalysts for Enantioselective Photo-Phosphoric Acid Catalysis.The Journal of organic chemistry · 2023Article
- Bidentate substrate binding in Brønsted acid catalysis: structural space, hydrogen bonding and dimerization.Chemical science · 2022Article
- Cooperative Stereoinduction in Asymmetric Photocatalysis.Journal of the American Chemical Society · 2022Article
- Enantioselective crossed intramolecular [2+2] photocycloaddition reactions mediated by a chiral chelating Lewis acid.Chemical science · 2022Article
- Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis.Chemical reviews · 2022Review
- Syntheses of new chiral chimeric photo-organocatalysts.RSC advances · 2021Article
- Enantioselective [2 + 2] Photocycloaddition via Iminium Ions: Catalysis by a Sensitizing Chiral Brønsted Acid.Journal of the American Chemical Society · 2021Article
- Recent Visible Light and Metal Free Strategies in [2+2] and [4+2] Photocycloadditions.European journal of organic chemistry · 2021Review
- Visible-Light-Mediated Heterocycle Functionalization via Geometrically Interrupted [2+2] Cycloaddition.Angewandte Chemie (International ed. in English) · 2020Article
- Visible Light-Mediated Photochemical Reactions of 2-(2'-Alkenyloxy)cycloalk-2-enones.The Journal of organic chemistry · 2020Article
- A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light-Mediated Cycloadditions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Recent developments in enantioselective photocatalysis.Beilstein journal of organic chemistry · 2020Review
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
A chiral phosphoric acid with a 2,2'-binaphthol core was prepared that displays two thioxanthone moieties at the 3,3'-position as light-harvesting antennas. Despite its relatively low triplet energy, the phosphoric acid was found to be an efficient catalyst for the enantioselective intermolecular [2+2] photocycloaddition of β-carboxyl-substituted cyclic enones (e.r. up to 93:7). Binding of the carboxylic acid to the sensitizer is suggested by NMR studies and by DFT calculations to occur by means of two hydrogen bonds. The binding event not only enables an enantioface differentiation but also modulates the triplet energy of the substrates.
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Registered trials
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