ArticleNature chemistry2020
Stereoselective access to [5.5.0] and [4.4.1] bicyclic compounds through Pd-catalysed divergent higher-order cycloadditions.
Article in Nature chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Template-assisted [6+6] cycloaddition for the construction of photothermally responsive functional materials.Nature communications · 2026Article
- Catalytic asymmetric tandem Heck/Sonogashira reaction enabling access to versatile chiral bridged ring scaffolds.Nature communications · 2025Article
- Divergent access to E- or Z-trisubstituted medium-sized cycloalkenes by Pd-catalysed cycloaddition.Nature chemistry · 2025Article
- Cycloaddition and functionalization reactions involving tropone.RSC advances · 2025Review
- Theoretical Studies on the Reaction Mechanism for the Cycloaddition of Zwitterionic π-Allenyl Palladium Species: Substrate-Controlled Isomerization.Molecules (Basel, Switzerland) · 2024Article
- Article
- Organocatalytic diastereo- and atropo-selective construction of eight-membered bridged (hetero)biarylsChemical science · 2024Article
- Recent Advances in Palladium-Catalyzed [4 + n] Cycloaddition of Lactones, Benzoxazinanones, Allylic Carbonates, and Vinyloxetanes.Topics in current chemistry (Cham) · 2023Review
- Chemodivergence in Pd-catalyzed desymmetrization of allenes: enantioselective [4+3] cycloaddition, desymmetric allenylic substitution and enynylation.Chemical science · 2023Article
- Fungicide-inspired precursors of π-allylpalladium intermediates for palladium-catalyzed decarboxylative cycloadditions.Chemical science · 2023Article
- Asymmetric higher-order [10 +Chemical science · 2022Article
- Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes.Nature communications · 2021Article
- Combining palladium and ammonium halide catalysts for Morita-Baylis-Hillman carbonates of methyl vinyl ketone: from 1,4-carbodipoles to ion pairs.Chemical science · 2021Article
Corrections and comments
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Authors and funding
10 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Medium-sized rings, including those embedded in bridged and fused bicyclic scaffolds, are common core structures of myriad bioactive molecules. Among various synthetic strategies towards their synthesis, intermolecular higher-order cycloaddition provides great potential to build complex medium-sized rings from simple building blocks. Unfortunately, such transformations are often plagued with competitive reaction pathways and low levels of site- and stereoselectivity. Herein, we report catalyst-controlled divergent access to three classes of medium-sized bicyclic compounds in high efficiency and stereoselectivity, by palladium-catalysed cycloadditions of tropones with γ-methylidene-δ-valerolactones. Mechanistic studies and density functional theory calculations disclosed that the divergent reactions stem from the different reaction profiles of the diastereomeric intermediates. While one undergoes either O- or C-allylation to provide [5.5.0] or [4.4.1] bicyclic compounds, the unique conformation of the other diastereomer allows an unconventional alkene isomerization to deliver bridgehead alkene-containing bicyclo[4.4.1] compounds. The conversion of these products to diverse complex polycyclic scaffolds has also been demonstrated.
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Registered trials
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