ArticleJournal of the American Chemical Society2023
Catalytic Enantioselective 6π Photocyclization of Acrylanilides.
Article in Journal of the American Chemical Society, 2023. 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, 42 citations in OpenAlex.
- Probing Into Asymmetric Dearomatizing Photocycloadditions of 2-Naphthalene Derivatives With Alkenes: [2 + 2] and [4 + 2] Pathways.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Enantioselective [6π] Photocyclization Reactions by Chromophore Activation with a Chiral Lewis Acid.Journal of the American Chemical Society · 2025Article
- Energy transfer-enabled enantioselective photocyclization using a privileged Al-salen catalyst.Nature chemistry · 2025Article
- Privileged Chiral Photocatalysts.Angewandte Chemie (International ed. in English) · 2025Review
- Redox-innocent scandium(III) as the sole catalyst in visible light photooxidations.Nature communications · 2025Article
- Article
- Regiodivergent Ring-Expansion of Oxindoles to Quinolinones.Journal of the American Chemical Society · 2024Article
- Highly Enantioselective 6π Photoelectrocyclizations Engineered by Hydrogen Bonding.Journal of the American Chemical Society · 2023Article
- A Lewis Acid-Controlled Enantiodivergent Epoxidation of Aldehydes.ACS catalysis · 2023Article
- Investigating the Effect of Lewis Acid Co-catalysts on Photosensitized Visible-Light De Mayo Reactions.Organic letters · 2023Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Controlling absolute stereochemistry in catalytic photochemical reactions is generally challenging owing to high rates of background reactivity. Successful strategies broadly rely on selective excitation of the reaction substrate when associated with a chiral catalyst. Recent studies have demonstrated that chiral Lewis acid complexes can enable selective energy transfer from a photosensitizer to facilitate enantioselective triplet state reactions. Here, we apply this approach to the enantioselective catalysis of a 6π photocyclization through the design of an iridium photosensitizer optimized to undergo energy transfer to a reaction substrate only in the presence of a chiral Lewis acid complex. Among a group of iridium(III) sensitizers, enantioselectivity and yield closely correlate with photocatalyst triplet energy within a narrow window enabled by a modest reduction in substrate triplet energy upon binding a scandium/ligand complex. These results demonstrate that photocatalyst tuning offers a means to suppress background reactivity and improve enantioselectivity in photochemical reactions.
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