ArticleJournal of the American Chemical Society2019
Enantioselective Intermolecular Excited-State Photoreactions Using a Chiral Ir Triplet Sensitizer: Separating Association from Energy Transfer in Asymmetric Photocatalysis.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 47 papers.
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Who cites it
47 citing papers in PubMed.
- Excitation of acyclic trisubstituted alkenes via triplet energy transfer for diastereo- and enantioselective [2 + 2] photocycloaddition.Nature communications · 2026Article
- Red light mediated energy transfer catalysisChemical science · 2026Article
- Modulating endergonic triplet photosensitization for cycloadditions between bicyclo[1.1.0]butanes and alkenes.Nature chemistry · 2026Article
- Substrate-Affinitive P-Type Azapolycyclic Photosensitizer for Chemoselective Nitrilization Under Mild Conditions.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Bifunctional Photocatalysts: Exploiting Proximity for Enhanced Reaction Performance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Sulfonyl-Directed Photoinduced Dehydro-Diels-Alder Reaction of Aryl Maleimides: Enabling Regioselective Naphthalene Synthesis.JACS Au · 2026Article
- Privileged Chiral Photocatalysts.Angewandte Chemie (International ed. in English) · 2025Review
- Understanding the Mechanism of Triplet-Triplet Energy Transfer in the Photocatalytic [2 + 2] Cycloaddition: Insights From Quantum Chemical Modeling.Journal of computational chemistry · 2025Article
- Stereoselective Synthesis of Highly Functionalized Bicyclo[2.1.0]pentanes by Sequential [2 + 1] and [2 + 2] Cycloadditions.Organic letters · 2025Article
- Asymmetric synthesis of stereogenic-at-iridium(III) complexes through Pd-catalyzed kinetic resolution.Nature communications · 2025Article
- Oxetanes: formation, reactivity and total syntheses of natural products.Beilstein journal of organic chemistry · 2025Review
- Article
- Enantioselective Paternò-Büchi Reactions: Strategic Application of a Triplet Rebound Mechanism for Asymmetric Photocatalysis.Journal of the American Chemical Society · 2024Article
- Catalytic asymmetric [4 + 2] dearomative photocycloadditions of anthracene and its derivatives with alkenylazaarenes.Nature communications · 2024Article
- Organic Dye-Sensitized Nitrene Generation: Intermolecular Aziridination of Unactivated Alkenes.The Journal of organic chemistry · 2024Article
- Article
- Recent Progress in Free Radical Transformations of Allenamides.Current organic synthesis · 2024Article
- Highly Enantioselective 6π Photoelectrocyclizations Engineered by Hydrogen Bonding.Journal of the American Chemical Society · 2023Article
- Recent Advances in the Enantioselective Radical Reactions.Molecules (Basel, Switzerland) · 2023Review
- Photochemical [2 + 2] Cycloaddition of Alkenes with Maleimides: Highlighting the Differences betweenACS organic & inorganic Au · 2023Article
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8 authors.
Funding
Abstract
Enantioselective catalysis of excited-state photoreactions remains a substantial challenge in synthetic chemistry, and intermolecular photoreactions have proven especially difficult to conduct in a stereocontrolled fashion. Herein, we report a highly enantioselective intermolecular [2 + 2] cycloaddition of 3-alkoxyquinolones catalyzed by a chiral hydrogen-bonding iridium photosensitizer. Enantioselectivities as high as 99% ee were measured in reactions with a range of maleimides and other electron-deficient alkene reaction partners. An array of kinetic, spectroscopic, and computational studies supports a mechanism in which the photocatalyst and quinolone form a hydrogen-bonded complex to control selectivity, yet upon photoexcitation of this complex, energy transfer sensitization of maleimide is preferred. The sensitized maleimide then reacts with the hydrogen-bonded quinolone-photocatalyst complex to afford a highly enantioenriched cycloadduct. This finding contradicts a long-standing tenet of enantioselective photochemistry that held that stereoselective photoreactions require strong preassociation to the sensitized substrate in order to overcome the short lifetimes of electronically excited organic molecules. This system therefore suggests that a broader range of alternate design strategies for asymmetric photocatalysis might be possible.
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