ArticleScience (New York, N.Y.)2024
Enantioselective remote methylene C-H (hetero)arylation of cycloalkane carboxylic acids.
Article in Science (New York, N.Y.), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Ligand-Enabled Stereoselective Coupling of Methylene C(spAngewandte Chemie (International ed. in English) · 2026Article
- 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
- Review
- Intermolecular Enantioselective Nickel-Catalyzed Arylation of Un-Activated C(spAngewandte Chemie (International ed. in English) · 2026Article
- Enantioselective C-H Activation for the Construction of Chiral Tertiary Fluorides via Migrative Carbofluorination.Journal of the American Chemical Society · 2026Article
- Regiocontrollable [2 + 2] benzannulation of γ,δ-C(sp3)-H bonds with dihaloarenes using palladium catalysis.Nature synthesis · 2025Article
- The role of 1,4-palladium migration in C(spRSC advances · 2025Review
- From Mono-Accounts of chemical research · 2025Review
- Transition-Metal-Catalyzed C(spTopics in current chemistry (Cham) · 2025Review
- Molecular Machine Learning Approach to Enantioselective C-H Bond Activation Reactions: From Generative AI to Experimental Validation.Chemical science · 2025Article
- Impact of Induced Fitting and Secondary Noncovalent Interactions on Site-Selective and Enantioselective C-H Functionalization of Arylcyclohexanes.Journal of the American Chemical Society · 2025Article
- Synthesis of Chiral Carbocycles via Enantioselective β,γ-Dehydrogenation.Nature synthesis · 2024Article
- One-Step Synthesis of Chiral 9,10-Dihydrophenanthrenes via Ligand-Enabled Enantioselective Cascade β,γ-Diarylation of Acids.Angewandte Chemie (International ed. in English) · 2024Article
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Authors and funding
8 authors.
Funding
Abstract
Stereoselective construction of γ- and δ-stereocenters in carbonyl compounds is a pivotal objective in asymmetric synthesis. Here, we report chiral bifunctional oxazoline-pyridone ligands that enable enantioselective palladium-catalyzed remote γ-C-H (hetero)arylations of free cycloalkane carboxylic acids, which are essential carbocyclic building blocks in organic synthesis. The reaction establishes γ-tertiary and α-quaternary stereocenters simultaneously in up to >99% enantiomeric excess, providing access to a wide range of cyclic chiral synthons and bioactive molecules. The sequential enantioselective editing of two methylene C-H bonds can be achieved by using chiral ligands with opposite configuration to construct carbocycles containing three chiral centers. Enantioselective remote δ-C-H (hetero)arylation is also realized to establish δ-stereocenters that are particularly challenging to access using classical methodologies.
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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.