Articles producció científica> Química Analítica i Química Orgànica

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

  • Dades identificatives

    Identificador: imarina:6069429
    Autors:
    Scharnagel, DagmarEscofet, ImmaArmengol-Relats, HelenaElena de Orbe, M.Nepomuk Korber, J.Echavarren, Antonio M.
    Resum:
    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.
  • Altres:

    Autor segons l'article: Scharnagel, Dagmar; Escofet, Imma; Armengol-Relats, Helena; Elena de Orbe, M.; Nepomuk Korber, J.; Echavarren, Antonio M.;
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: ECHAVARREN PABLOS, ANTONIO
    Paraules clau: Total synthesis Intermolecular 2+2 cycloaddition Gold catalysis Cyclopropanation Constituents Alkynes Alkenes Acetylene gold catalysis cyclopropanation acetylene
    Resum: 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1433-7851
    Adreça de correu electrònic de l'autor: antoniomaria.echavarren@urv.cat
    Identificador de l'autor: 0000-0002-6418-7930
    Data d'alta del registre: 2022-07-23
    Volum de revista: 59
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201915895
    Referència a l'article segons font original: Angewandte Chemie (International Ed. Print). 59 (12): 4888-4891
    Referència de l'ítem segons les normes 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
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1002/anie.201915895
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2020
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Total synthesis
    Intermolecular 2+2 cycloaddition
    Gold catalysis
    Cyclopropanation
    Constituents
    Alkynes
    Alkenes
    Acetylene
    gold catalysis
    cyclopropanation
    acetylene
    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
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