ArticleNature chemistry2023
Access to unsaturated bicyclic lactones by overriding conventional C(sp
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
What it found
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The trial behind it
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Who cites it
10 citing papers in PubMed, 36 citations in OpenAlex.
- Asymmetric Total Synthesis of (+)-Ineleganolide.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Transition Metal-Catalyzed Direct C(spChemical reviews · 2026Review
- Synthesis of Spiro Carbocycles via Methyl β-C(spJournal of the American Chemical Society · 2026Article
- Migrating Group Strategy for Remote Functionalization of Seven-Membered Rings.Journal of the American Chemical Society · 2025Article
- A general leaving group assisted strategy for synthesis of pentafluorosulfanyl allylic compounds.Science advances · 2025Article
- Synthesis of Chiral Carbocycles via Enantioselective β,γ-Dehydrogenation.Nature synthesis · 2024Article
- Catalyst-Controlled Chemoselective γ-C(spJournal of the American Chemical Society · 2024Article
- Tandem dehydrogenation-olefination-decarboxylation of cycloalkyl carboxylic acids via multifold C-H activation.Nature communications · 2024Article
- Ligand-Enabled Double γ-C(spAngewandte Chemie (International ed. in English) · 2023Article
Corrections and comments
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Authors and funding
11 authors at 3 institutions in 3 countries.
Funding
Abstract
Transition metal catalysis plays a pivotal role in transforming unreactive C-H bonds. However, regioselective activation of distal aliphatic C-H bonds poses a tremendous challenge, particularly in the absence of directing templates. Activation of a methylene C-H bond in the presence of methyl C-H is underexplored. Here we show activation of a methylene C-H bond in the presence of methyl C-H bonds to form unsaturated bicyclic lactones. The protocol allows the reversal of the general selectivity in aliphatic C-H bond activation. Computational studies suggest that reversible C-H activation is followed by β-hydride elimination to generate the Pd-coordinated cycloalkene that undergoes stereoselective C-O cyclization, and subsequent β-hydride elimination to provide bicyclic unsaturated lactones. The broad generality of this reaction has been highlighted via dehydrogenative lactonization of mid to macro ring containing acids along with the C-H olefination reaction with olefin and allyl alcohol. The method substantially simplifies the synthesis of important bicyclic lactones that are important features of natural products as well as pharmacoactive molecules.
Identifiers
What OpenQuestion holds
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.