Articles producció científica> Química Física i Inorgànica

Stereoselective Cyclopropanation of 1,1-Diborylalkenes via Palladium-Catalyzed (Trimethylsilyl)diazomethane Insertion

  • Identification data

    Identifier: imarina:9280225
    Handle: https://hdl.handle.net/20.500.11797/imarina9280225
    Authors:
    Salvado, OriolDominguez-Molano, PaulaFernandez, Elena
    Abstract:
    Palladium catalyzes the cydclopropanation of 2-substituted 1,1-diborylalkenes with (trimethylsilyl)diazomethane. The relative stereoselectivity is controlled via a carbene insertion sequence generating an exclusive anti conformation between the R and SiMe3 substituents. Mixed 1,1-diborylalkenes also contributed to the formation of stereoselective B, B, Si-cyclopropanes. Orthogonal activation with (NaOBu)-Bu-t gives protodeborylation preferentially on the boron moiety syn to the aryl group. Further oxidation gives access to polyfunctional cycloopropyl alcohols with controlled enantioselectivity when chiral boryl motifs are involved.

  • Others:

    Author, as appears in the article.: Salvado, Oriol; Dominguez-Molano, Paula; Fernandez, Elena;
    Department: Química Física i Inorgànica
    URV's Author/s: Domínguez Molano, Paula / Fernández Gutiérrez, Maria Elena / Salvadó Ruiz, Oriol
    Keywords: Reagents Hydroboration Esters Carbenoids Asymmetric cyclopropanation Access
    Abstract: Palladium catalyzes the cydclopropanation of 2-substituted 1,1-diborylalkenes with (trimethylsilyl)diazomethane. The relative stereoselectivity is controlled via a carbene insertion sequence generating an exclusive anti conformation between the R and SiMe3 substituents. Mixed 1,1-diborylalkenes also contributed to the formation of stereoselective B, B, Si-cyclopropanes. Orthogonal activation with (NaOBu)-Bu-t gives protodeborylation preferentially on the boron moiety syn to the aryl group. Further oxidation gives access to polyfunctional cycloopropyl alcohols with controlled enantioselectivity when chiral boryl motifs are involved.
    Thematic Areas: Química Physical and theoretical chemistry Organic chemistry Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, organic Biotecnología Biodiversidade Biochemistry
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: oriol.salvado@urv.cat paula.dominguez@urv.cat paula.dominguez@urv.cat oriol.salvado@urv.cat mariaelena.fernandez@urv.cat
    Author identifier: 0000-0001-9025-1791
    Record's date: 2024-09-07
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.2c01885
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Organic Letters. 24 (27): 4949-4953
    APA: Salvado, Oriol; Dominguez-Molano, Paula; Fernandez, Elena; (2022). Stereoselective Cyclopropanation of 1,1-Diborylalkenes via Palladium-Catalyzed (Trimethylsilyl)diazomethane Insertion. Organic Letters, 24(27), 4949-4953. DOI: 10.1021/acs.orglett.2c01885
    Article's DOI: 10.1021/acs.orglett.2c01885
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2022
    Publication Type: Journal Publications

  • Keywords:

    Biochemistry,Chemistry, Organic,Organic Chemistry,Physical and Theoretical Chemistry
    Reagents
    Hydroboration
    Esters
    Carbenoids
    Asymmetric cyclopropanation
    Access
    Química
    Physical and theoretical chemistry
    Organic chemistry
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    Farmacia
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry, organic
    Biotecnología
    Biodiversidade
    Biochemistry

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