Articles producció científica> Química Física i Inorgànica

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

  • Datos identificativos

    Identificador: imarina:9280225
    Handle: https://hdl.handle.net/20.500.11797/imarina9280225
    Autores:
    Salvado, OriolDominguez-Molano, PaulaFernandez, Elena
    Resumen:
    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.

  • Otros:

    Autor según el artículo: Salvado, Oriol; Dominguez-Molano, Paula; Fernandez, Elena;
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: Domínguez Molano, Paula / Fernández Gutiérrez, Maria Elena / Salvadó Ruiz, Oriol
    Palabras clave: Reagents Hydroboration Esters Carbenoids Asymmetric cyclopropanation Access
    Resumen: 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.
    Áreas temáticas: 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
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: oriol.salvado@urv.cat paula.dominguez@urv.cat paula.dominguez@urv.cat oriol.salvado@urv.cat mariaelena.fernandez@urv.cat
    Identificador del autor: 0000-0001-9025-1791
    Fecha de alta del registro: 2024-09-07
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Organic Letters. 24 (27): 4949-4953
    Referencia de l'ítem segons les normes 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
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2022
    Tipo de publicación: Journal Publications

  • Palabras clave:

    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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