ArticleJournal of the American Chemical Society2024
Enantioselective Paternò-Büchi Reactions: Strategic Application of a Triplet Rebound Mechanism for Asymmetric Photocatalysis.
Article in Journal of the American Chemical Society, 2024. 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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Who cites it
10 citing papers in PubMed.
- Excitation of acyclic trisubstituted alkenes via triplet energy transfer for diastereo- and enantioselective [2 + 2] photocycloaddition.Nature communications · 2026Article
- Substituent-rebound skeletal editing for precise boron-to-carbon single-atom swapping.Nature communications · 2026Article
- Triplet Energy Transfer-Mediated Intermolecular Paternò-Büchi Reaction for the Synthesis of Trifluoromethylated Oxetanes.Organic letters · 2026Article
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Design of a combined LED and rapid-injection NMR system for structure elucidations and kinetic analyses.Nature communications · 2025Article
- Privileged Chiral Photocatalysts.Angewandte Chemie (International ed. in English) · 2025Review
- Energy transfer-enabled enantioselective photocyclization using a privileged Al-salen catalyst.Nature chemistry · 2025Article
- Oxetane Cleavage Pathways in the Excited State: Photochemical Kinetic Resolution as an Approach to Enantiopure Oxetanes.Journal of the American Chemical Society · 2025Article
- Oxetanes: formation, reactivity and total syntheses of natural products.Beilstein journal of organic chemistry · 2025Review
- Visible-light-mediated deoxygenative transformation of 1,2-dicarbonyl compounds through energy transfer process.Nature communications · 2024Article
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Authors and funding
9 authors.
Funding
Abstract
The Paternò-Büchi reaction is the [2 + 2] photocycloaddition of a carbonyl with an alkene to afford an oxetane. Enantioselective catalysis of this classical photoreaction, however, has proven to be a long-standing challenge. Many of the best-developed strategies for asymmetric photochemistry are not suitable to address this problem because the interaction of carbonyls with Brønsted or Lewis acidic catalysts can alter the electronic structure of their excited state and divert their reactivity toward alternate photoproducts. We show herein that a triplet rebound strategy enables the stereocontrolled reaction of an excited-state carbonyl compound in its native, unbound state. These studies have resulted in the development of the first highly enantioselective catalytic Paternò-Büchi reaction, catalyzed by a novel hydrogen-bonding chiral Ir photocatalyst.
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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.