ArticleAngewandte Chemie (International ed. in English)2021
Switchable, Reagent-Controlled Diastereodivergent Photocatalytic Carbocyclisation of Imine-Derived α-Amino Radicals.
Article in Angewandte Chemie (International ed. in English), 2021. 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.
- Acridine/Lewis acid photocatalysis enables α-amidyl radical cyclizations.Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Methyl Radical Addition Reactions to C═X Double Bonds.The Journal of organic chemistry · 2025Article
- Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework.Nature communications · 2024Article
- Photocascade chemoselective controlling of ambident thio(seleno)cyanates with alkenes via catalyst modulation.Nature communications · 2024Article
- Straightforward synthesis of functionalized γ-Lactams using impure CONature communications · 2023Article
- Article
- Photoredox Activation of Anhydrides for the Solvent-Controlled Switchable Synthesis of gem-Difluoro Compounds.Angewandte Chemie (International ed. in English) · 2022Article
- Recent advances in visible light-induced C(Nature reviews. Chemistry · 2022Article
- Switchable Regioselective 6-Journal of the American Chemical Society · 2022Article
- Switchable, Reagent-Controlled Diastereodivergent Photocatalytic Carbocyclisation of Imine-Derived α-Amino Radicals.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
7 authors.
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Abstract
A reagent-controlled stereodivergent carbocyclisation of aryl aldimine-derived, photocatalytically generated, α-amino radicals possessing adjacent conjugated alkenes, affording either bicyclic or tetracyclic products, is described. Under net reductive conditions using commercial Hantzsch ester, the α-amino radical species underwent a single stereoselective cyclisation to give trans-configured amino-indane structures in good yield, whereas using a substituted Hantzsch ester as a milder reductant afforded cis-fused tetracyclic tetrahydroquinoline frameworks, resulting from two consecutive radical cyclisations. Judicious choice of the reaction conditions allowed libraries of both single and dual cyclisation products to be synthesised with high selectivity, notable predictability, and good-to-excellent yields. Computational analysis employing DFT revealed the reaction pathway and mechanistic rationale behind this finely balanced yet readily controlled photocatalytic system.
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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.