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, R; Fernández, E
    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, R; Fernández, E (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: 2019-06-18
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/acceptedVersion
    Record's date: 2026-05-09
    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, R; Fernández, E
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Organic chemistry, General medicine, General chemistry, Chemistry, multidisciplinary, Chemistry (miscellaneous), Chemistry (all), Chemistry, Catalysis, Biotecnología, Biodiversidade
    Author's mail: mariaelena.fernandez@urv.cat, 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
    General medicine
    General chemistry
    Chemistry (all)
    Biotecnología
    Biodiversidade

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