Articles producció científicaQuímica Física i Inorgànica

Selective C-C coupling of vinyl epoxides with diborylmethide lithium salts

  • Identification data

    Identifier:  imarina:5133299
    Handle: https://hdl.handle.net/20.500.11797/imarina5133299
    Authors:  Gava, Riccardo; Fernandez, Elena
    Abstract:
    © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Vinyl epoxides and styrene oxide can react with diborylmethide lithium salts through an exclusive SN2 borylmethylation/ring opening in a regio- and diastereoselective way, depending on the nature of the substrate. The ring-opening protocol provides homoallylboronates that can be transformed into challenging diastereomeric bishomoallylic alicyclic 1,3-diols. Unprecedented 3-borylated 1,2-oxaborolan-2-ol products were prepared by borylmethylation/ring opening of 2-methyl-2-vinyloxirane followed by intramolecular cyclization.

  • Others:

    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201901406
    APA: Gava, Riccardo; Fernandez, Elena (2019). Selective C-C coupling of vinyl epoxides with diborylmethide lithium salts. Chemistry-A European Journal, 25(34), 8013-8017. DOI: 10.1002/chem.201901406
    Paper original source: Chemistry-A European Journal. 25 (34): 8013-8017
    Article's DOI: 10.1002/chem.201901406
    Journal publication year: 2019
    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: 15213765
    Author, as appears in the article.: Gava, Riccardo; Fernandez, Elena
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Química, Organic chemistry, Medicina i, Materiais, Interdisciplinar, General medicine, General chemistry, Farmacia, Engenharias iii, Engenharias ii, Ciências biológicas iii, Ciências biológicas ii, Ciências biológicas i, Ciências agrárias i, Chemistry, multidisciplinary, Chemistry (miscellaneous), Chemistry (all), Chemistry, Catalysis, Biotecnología, Biodiversidade, Astronomia / física
    Author's mail: mariaelena.fernandez@urv.cat

  • Keywords:

    Sn2 mechanism
    S(n)2 mechanism
    S 2 mechanism n
    Lithium salts
    Ketones
    Insertion
    Homoallylboronates
    Geminal diborylalkanes
    Gem-silylborylation
    Esters
    Diborylalkanes
    Diboronates
    Deprotonation
    Carbanions
    Alkyl-halides
    Aldehydes
    Access
    Catalysis
    Chemistry
    Chemistry (Miscellaneous)
    Multidisciplinary
    Organic Chemistry
    Química
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias iii
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry (all)
    Biotecnología
    Biodiversidade
    Astronomia / física

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