Articles producció científica> Química Física i Inorgànica

Catalytic Stereoselective Borylative Transannular Reactions

  • Identification data

    Identifier: imarina:6013697
    Authors:
    Sendra, JanaManzano, RubenReyes, EfraimVicario, 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:

    Author, as appears in the article.: Sendra, Jana; Manzano, Ruben; Reyes, Efraim; Vicario, Jose L.; Fernandez, Elena;
    Department: Química Física i Inorgànica
    URV's Author/s: Fernández Gutiérrez, Maria Elena
    Keywords: Transannular borylation Stereogenic alkyl boronate Ring closing Esters Electrophilic intramolecular trapping Cyclization Copper(i)-catalyzed reaction Copper catalysts stereogenic alkyl boronate ring closing electrophilic intramolecular trapping copper catalysts
    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.
    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
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 14337851
    Author's mail: mariaelena.fernandez@urv.cat
    Author identifier: 0000-0001-9025-1791
    Record's date: 2023-02-18
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201913438
    Papper original source: Angewandte Chemie (International Ed. Print). 59 (5): 2100-2104
    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
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1002/anie.201913438
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2020
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Transannular borylation
    Stereogenic alkyl boronate
    Ring closing
    Esters
    Electrophilic intramolecular trapping
    Cyclization
    Copper(i)-catalyzed reaction
    Copper catalysts
    stereogenic alkyl boronate
    ring closing
    electrophilic intramolecular trapping
    copper catalysts
    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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