ArticleAngewandte Chemie (International ed. in English)2022
Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Radical enantioconvergent meta-C─H alkylation of pyridines.Science advances · 2026Article
- Phosphonium Ions as Activating Groups for the Selective Alkylation of Pyridines and Polyazines.Journal of the American Chemical Society · 2026Article
- Room-temperature electrochemical hydroxyalkylation of pyridines.Nature communications · 2026Article
- Oxidant-free cross-dehydrogenative oxyalkylation enables late-stage functionalization of drugs.Innovation (Cambridge (Mass.)) · 2025Article
- Catalytic Enantioselective C-C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents.Chemical reviews · 2024Review
- Photocatalytic Enantioselective Radical Cascade Multicomponent Minisci Reaction of β-Carbolines Using Diazo Compounds as Radical Precursors.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis.The Journal of organic chemistry · 2023Article
- Recent Advances in the Enantioselective Radical Reactions.Molecules (Basel, Switzerland) · 2023Review
- Recent Advances in C-H Functionalisation through Indirect Hydrogen Atom Transfer.Molecules (Basel, Switzerland) · 2023Review
- Discovery and Development of the Enantioselective Minisci Reaction.Accounts of chemical research · 2023Article
- Regioselective Radical Alkylation of Arenes Using Evolved Photoenzymes.Journal of the American Chemical Society · 2023Article
- Regioselective Radical Alkylation of Arenes Using Evolved Photoenzymes.Research square · 2023Article
- Photocatalytic enantioselective Minisci reaction of β-carbolines and application to natural product synthesis.Chemical science · 2023Article
- Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C-H Bonds.Journal of the American Chemical Society · 2022Review
- A switchable redox annulation of 2-nitroarylethanols affordingChemical science · 2022Article
- Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
7 authors.
Funding
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Abstract
Catalytic enantioselective Minisci reactions have recently been developed but all instances so far utilize α-amino radical coupling partners. We report a substantial evolution of the enantioselective Minisci reaction that enables α-hydroxy radicals to be used, providing valuable enantioenriched secondary alcohol products. This is achieved through the direct oxidative coupling of two C-H bonds on simple alcohol and pyridine partners through a hydrogen atom transfer (HAT)-driven approach: a challenging process to achieve due to the numerous side reactions that can occur. Our approach is highly regioselective as well as highly enantioselective. Dicumyl peroxide, upon irradiation with 390 nm light, serves as both HAT reagent and oxidant whilst selectivity is controlled by use of a chiral phosphoric acid catalyst. Computational and experimental evidence provide mechanistic insight as to the origin of selectivity, revealing a stereodetermining deprotonation step distinct from the analogous reaction of amide-containing substrates.
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