ArticleJournal of the American Chemical Society2022
Carboxylic Acid Directed γ-Lactonization of Unactivated Primary C-H Bonds Catalyzed by Mn Complexes: Application to Stereoselective Natural Product Diversification.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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19 citing papers in PubMed, 58 citations in OpenAlex.
- Transition Metal-Catalyzed Direct C(spChemical reviews · 2026Review
- Desymmetrization of Malonic Monoesters and Malonic Acids via Enantioselective Catalytic C(spAngewandte Chemie (International ed. in English) · 2026Article
- Enantioselective Synthesis of Spirolactones and Spirolactams Under Low Catalyst Loadings.Journal of the American Chemical Society · 2026Article
- Photocatalytic Stereoselective Editing of Alkynes to 3D Molecules via Hydrogen Atom Transfer-Mediated Dynamic Epimerization.Nature communications · 2026Article
- Asymmetric Hydrogen Atom Transfer.ACS catalysis · 2026Review
- Catalytic Dioxygen Activation Using a Diketopiperazine and a Manganese Catalyst for Selective C(spJACS Au · 2025Article
- Manganese-Catalyzed Enantioselective Dearomative Epoxidation of Naphthalenes with Aqueous Hydrogen Peroxide.Angewandte Chemie (International ed. in English) · 2025Article
- Understanding Catalytic Enantioselective C-H Bond Oxidation at Nonactivated Methylenes Through Predictive Statistical Modeling Analysis.ACS catalysis · 2025Article
- Chiral Bis-8-Aryl-isoquinoline Bis-alkylamine Iron Catalysts for Asymmetric Oxidation Reactions.Organic letters · 2025Article
- Substitution, Elimination, and Integration of Methyl Groups in Terpenes Initiated by C-H Bond Functionalization.ACS central science · 2024Article
- C-H functionalization of camphor through emerging approaches.Chemistry letters · 2024Review
- Catalyst-Controlled Chemoselective γ-C(spJournal of the American Chemical Society · 2024Article
- Intramolecular C-H Oxidation in Iron(V)-oxo-carboxylato Species Relevant in the γ-Lactonization of Alkyl Carboxylic Acids.ACS catalysis · 2024Article
- Versatile Copper-Catalyzed γ-C(spJournal of the American Chemical Society · 2024Article
- Catalyst and Medium Control over Rebound Pathways in Manganese-Catalyzed Methylenic C-H Bond Oxidation.Journal of the American Chemical Society · 2024Article
- Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and - lactams.Chemical science · 2024Article
- Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-International journal of molecular sciences · 2024Article
- Highly Enantioselective Catalytic Lactonization at Nonactivated Primary and SecondaryJournal of the American Chemical Society · 2023Article
- C-H Bonds as Functional Groups: Simultaneous Generation of Multiple Stereocenters by Enantioselective Hydroxylation at Unactivated Tertiary C-H Bonds.Journal of the American Chemical Society · 2023Article
Corrections and comments
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Authors and funding
10 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Reactions that enable selective functionalization of strong aliphatic C-H bonds open new synthetic paths to rapidly increase molecular complexity and expand chemical space. Particularly valuable are reactions where site-selectivity can be directed toward a specific C-H bond by catalyst control. Herein we describe the catalytic site- and stereoselective γ-lactonization of unactivated primary C-H bonds in carboxylic acid substrates. The system relies on a chiral Mn catalyst that activates aqueous hydrogen peroxide to promote intramolecular lactonization under mild conditions, via carboxylate binding to the metal center. The system exhibits high site-selectivity and enables the oxidation of unactivated primary γ-C-H bonds even in the presence of intrinsically weaker and a priori more reactive secondary and tertiary ones at α- and β-carbons. With substrates bearing nonequivalent γ-C-H bonds, the factors governing site-selectivity have been uncovered. Most remarkably, by manipulating the absolute chirality of the catalyst, γ-lactonization at methyl groups in
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