ArticleJournal of the American Chemical Society2016
Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.
Article in Journal of the American Chemical Society, 2016. 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.
- Organocatalytic Enantioselective [4 + 4] Cycloadditions of Furan Ortho-Quinodimethanes.Angewandte Chemie (International ed. in English) · 2025Article
- Catalyst-free and wavelength-tuned glycosylation based on excited-state intramolecular proton transfer.Nature communications · 2024Article
- Complexity-Building ESIPT-Assisted Synthesis of Fused Polyheterocyclic Sulfonamides.Molecules (Basel, Switzerland) · 2023Article
- Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B.Chemical science · 2021Article
- Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems.RSC advances · 2019Article
- Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-Journal of the American Chemical Society · 2019Article
- Photoinitiated Cascade for Rapid Access to Pyrroloquinazolinone Core of Vasicinone, Luotonins, and Related Alkaloids.Organic letters · 2019Article
- Ti(Oi-Pr)Nature communications · 2017Article
- Photoassisted access to complex polyheterocycles containing a β-lactam moiety.Journal of photochemistry and photobiology. A, Chemistry · 2016Article
- Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts.Journal of the American Chemical Society · 2016Article
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Authors and funding
2 authors.
Funding
Abstract
2-(o-Amidophenyl)oxa- and -thiazolines undergo excited-state intramolecular proton transfer (ESIPT), generating aza-o-xylylenes capable of intramolecular [4+2] and [4+4] cycloadditions with tethered unsaturated pendants. Facile hydrolysis of the primary photoproducts, spiro-oxazolidines and thiazolidines, under mild conditions unmasks a phenone functionality. Variations in linkers allow for access to diverse core scaffolds in the primary photoproducts, rendering the approach compatible with the philosophy of diversity-oriented synthesis. Chiral oxazolines, readily available from the corresponding amino alcohols, yield enantioenriched keto-polyheterocycles of complex topologies with enantiomeric excess values up to 90%.
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