Articles producció científicaQuímica Física i Inorgànica

Catalytic Stereoselective Borylative Transannular Reactions

  • Identification data

    Identifier:  imarina:6013697
    Handle: https://hdl.handle.net/20.500.11797/imarina6013697
    Authors:  Sendra, Jana; Manzano, Ruben; Reyes, Efraim; Vicario, Jose L; Fernandez, Elena
    Abstract:
    Medium-sized carbocycles containing an alpha,beta-unsaturated ketone moiety as Michael acceptor site and a ketone moiety as internal electrophilic site are ideal substrates to conduct Cu(I)-catalyzed conjugated borylation followed by electrophilic intramolecular trapping that results into a pioneer transannular borylative ring closing reaction. The relative configuration of three adjacent stereocenters is controlled, giving access to a single diastereoisomer for a wide range of substrates tested. Moreover, when a chiral ligand is incorporated, the reaction provides enantioenriched polycyclic products with up to 99 % ee.

  • Others:

    Link to the original source: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201913438
    APA: Sendra, Jana; Manzano, Ruben; Reyes, Efraim; Vicario, Jose L; Fernandez, Elena (2020). Catalytic Stereoselective Borylative Transannular Reactions. Angewandte Chemie (International Ed. Print), 59(5), 2100-2104. DOI: 10.1002/anie.201913438
    Paper original source: Angewandte Chemie (International Ed. Print). 59 (5): 2100-2104
    Article's DOI: 10.1002/anie.201913438
    Journal publication year: 2020
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/acceptedVersion
    Record's date: 2025-02-18
    URV's Author/s: Fernández Gutiérrez, Maria Elena
    Department: Química Física i Inorgànica
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Journal Publications
    ISSN: 14337851
    Author, as appears in the article.: Sendra, Jana; Manzano, Ruben; Reyes, Efraim; Vicario, Jose L; Fernandez, Elena
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    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: mariaelena.fernandez@urv.cat

  • Keywords:

    Transannular borylation
    Stereogenic alkyl boronate
    Ring closing
    Esters
    Electrophilic intramolecular trapping
    Cyclization
    Copper(i)-catalyzed reaction
    Copper catalysts
    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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