Articles producció científica> Química Analítica i Química Orgànica

Photoredox Organocatalysis for the Enantioselective Synthesis of 1,7-Dicarbonyl Compounds

  • Datos identificativos

    Identificador: imarina:9247329
    Handle: https://hdl.handle.net/20.500.11797/imarina9247329
    Autores:
    Wong THFMa DDi Sanza RMelchiorre P
    Resumen:
    We describe an asymmetric organocatalytic method to synthesize 1,7-dicarbonyl compounds containing a β-stereocenter. The chemistry relies on the formation of γ-keto radicals, generated upon oxidative ring opening of cyclobutanols mastered by an organic photoredox catalyst. These nonstabilized primary radicals are stereoselectively intercepted by an iminium ion intermediate, formed upon activation of aliphatic and aromatic enals by a chiral secondary amine catalyst. This organocatalytic photoredox method served to prepare scaffolds found in natural products and drug molecules.

  • Otros:

    Autor según el artículo: Wong THF; Ma D; Di Sanza R; Melchiorre P
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: Wong, Thomas Hin-Fung
    Palabras clave: Bond-cleavage strategy receptor enables cycloalkanols
    Resumen: We describe an asymmetric organocatalytic method to synthesize 1,7-dicarbonyl compounds containing a β-stereocenter. The chemistry relies on the formation of γ-keto radicals, generated upon oxidative ring opening of cyclobutanols mastered by an organic photoredox catalyst. These nonstabilized primary radicals are stereoselectively intercepted by an iminium ion intermediate, formed upon activation of aliphatic and aromatic enals by a chiral secondary amine catalyst. This organocatalytic photoredox method served to prepare scaffolds found in natural products and drug molecules.
    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: thomashin-fung.wong@estudiants.urv.cat
    Identificador del autor: 0000-0002-5729-9619
    Fecha de alta del registro: 2024-09-07
    Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
    Enlace a la fuente original: https://pubs.acs.org/doi/10.1021/acs.orglett.2c00326#
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Organic Letters. 24 (8): 1695-1699
    Referencia de l'ítem segons les normes APA: Wong THF; Ma D; Di Sanza R; Melchiorre P (2022). Photoredox Organocatalysis for the Enantioselective Synthesis of 1,7-Dicarbonyl Compounds. Organic Letters, 24(8), 1695-1699. DOI: 10.1021/acs.orglett.2c00326
    DOI del artículo: 10.1021/acs.orglett.2c00326
    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
    Bond-cleavage
    strategy
    receptor
    enables
    cycloalkanols
    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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