ArticleJournal of the American Chemical Society2018
Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 60 papers.
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60 citing papers in PubMed, 247 citations in OpenAlex.
- Catalytic Asymmetric Dearomative Cyclizations of Indolyldimethanols via Umpolung Strategy.JACS Au · 2026Article
- Vicinal disubstitution of alkyl C-X synthons via alkene radical cation generation.Science (New York, N.Y.) · 2026Article
- Electrochemical Activation of α-Carbonyl Alkoxyamines for Direct Nucleophilic Substitution.Organic letters · 2026Article
- Characterisation of the N-Methyltransferase SgPsmC: Application in the Kinetic Resolution of Pyrroloindolines.Angewandte Chemie (International ed. in English) · 2026Article
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- An anion-binding approach to enantioselective photoredox catalysis.Science (New York, N.Y.) · 2025Article
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- Natural Product Synthesis Enabled by Radical-Polar Crossover Reactions.The Journal of organic chemistry · 2025Review
- Verticillins: fungal epipolythiodioxopiperazine alkaloids with chemotherapeutic potential.Natural product reports · 2024Review
- Photochemical dearomative skeletal modifications of heteroaromatics.Chemical Society reviews · 2024Review
- Tunable C-H functionalization and dearomatization enabled by an organic photocatalyst.Chemical science · 2024Article
- Efficient construction of functionalized pyrroloindolines through cascade radical cyclization/intermolecular coupling.Chemical science · 2024Article
- Photoenzymatic Enantioselective Intermolecular Radical Hydroamination.Nature catalysis · 2023Article
- Mechanistic duality of indolyl 1,3-heteroatom transposition.Chemical science · 2023Article
- Computational molecular refinement to enhance enantioselectivity by reinforcing hydrogen bonding interactions in major reaction pathway.Chemical science · 2023Article
- Aqueous Flavin Photoredox Catalysis Drives Exclusive C3-Alkylation of Indolyl Radical Cations in Route to Unnatural Tryptophan Mimetics.Organic letters · 2023Article
- Combining photoredox catalysis and hydrogen atom transfer for dearomative functionalization of electron rich heteroarenes.Chemical science · 2023Article
- Light-driven redox deracemization of indolines and tetrahydroquinolines using a photocatalyst coupled with chiral phosphoric acid.Chemical science · 2023Article
- Atroposelective Synthesis of 2,2'-Bis(arylamino)-1,1'-biaryls by Oxidative Iron(III)- and Phosphoric Acid-Catalyzed C-C Coupling of Diarylamines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications.Chemical reviews · 2023Review
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Authors and funding
5 authors at 1 institution in 1 country.
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Abstract
While interest in the synthetic chemistry of radical cations continues to grow, controlling enantioselectivity in the reactions of these intermediates remains a challenge. Based on recent insights into the oxidation of tryptophan in enzymatic systems, we report a photocatalytic method for the generation of indole radical cations as hydrogen-bonded adducts with chiral phosphate anions. These noncovalent open-shell complexes can be intercepted by the stable nitroxyl radical TEMPO· to form alkoxyamine-substituted pyrroloindolines with high levels of enantioselectivity. Further elaboration of these optically enriched adducts can be achieved via a catalytic single-electron oxidation/mesolytic cleavage sequence to furnish transient carbocation intermediates that may be intercepted by a wide range of nucleophiles. Taken together, this two-step sequence provides a simple catalytic method to access a wide range of substituted pyrroloindolines in enantioenriched form via a standard experimental protocol from a common synthetic intermediate. The design, development, mechanistic study, and scope of this process are presented, as are applications of this method to the synthesis of several dimeric pyrroloindoline natural products.
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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.