Articles producció científicaQuímica Analítica i Química Orgànica

Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step

  • Identification data

    Identifier:  imarina:6069429
    Handle: https://hdl.handle.net/20.500.11797/imarina6069429
    Authors:  Scharnagel, Dagmar; Escofet, Imma; Armengol-Relats, Helena; Elena de Orbe, M; Nepomuk Korber, J; Echavarren, Antonio M
    Abstract:
    The gold(I)-catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)-1,4-disubstituted 1,3-butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user-friendly procedure. Reaction of acetylene with 1,5-dienes gives rise stereoselectively to tricyclo[5.1.0.0(2,4)]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.

  • Others:

    Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201915895
    APA: Scharnagel, Dagmar; Escofet, Imma; Armengol-Relats, Helena; Elena de Orbe, M; Nepomuk Korber, J; Echavarren, Antonio M (2020). Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step. Angewandte Chemie (International Ed. Print), 59(12), 4888-4891. DOI: 10.1002/anie.201915895
    Paper original source: Angewandte Chemie (International Ed. Print). 59 (12): 4888-4891
    Article's DOI: 10.1002/anie.201915895
    Journal publication year: 2020
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/publishedVersion
    Record's date: 2025-02-18
    URV's Author/s: ECHAVARREN PABLOS, ANTONIO
    Department: Química Analítica i Química Orgànica
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Journal Publications
    ISSN: 1433-7851
    Author, as appears in the article.: Scharnagel, Dagmar; Escofet, Imma; Armengol-Relats, Helena; Elena de Orbe, M; Nepomuk Korber, J; Echavarren, Antonio M
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Journal volume: 59
    Thematic Areas: Química, Medicina ii, Medicina i, Materiais, Interdisciplinar, General medicine, General chemistry, Farmacia, Engenharias ii, Ciências biológicas iii, Ciências biológicas ii, Ciências biológicas i, Chemistry, multidisciplinary, Chemistry (miscellaneous), Chemistry (all), Chemistry, Catalysis, Astronomia / física
    Author's mail: antoniomaria.echavarren@urv.cat

  • Keywords:

    Total synthesis
    Intermolecular 2+2 cycloaddition
    Gold catalysis
    Cyclopropanation
    Constituents
    Alkynes
    Alkenes
    Acetylene
    Catalysis
    Chemistry
    Chemistry (Miscellaneous)
    Multidisciplinary
    Química
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Chemistry (all)
    Astronomia / física

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