Articles producció científica> Química Analítica i Química Orgànica

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

  • Dades identificatives

    Identificador: imarina:9247329
    Handle: https://hdl.handle.net/20.500.11797/imarina9247329
    Autors:
    Wong THFMa DDi Sanza RMelchiorre P
    Resum:
    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.

  • Altres:

    Autor segons l'article: Wong THF; Ma D; Di Sanza R; Melchiorre P
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: Wong, Thomas Hin-Fung
    Paraules clau: Bond-cleavage strategy receptor enables cycloalkanols
    Resum: 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: thomashin-fung.wong@estudiants.urv.cat
    Identificador de l'autor: 0000-0002-5729-9619
    Data d'alta del registre: 2024-09-07
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://pubs.acs.org/doi/10.1021/acs.orglett.2c00326#
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Organic Letters. 24 (8): 1695-1699
    Referència 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 de l'article: 10.1021/acs.orglett.2c00326
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2022
    Tipus de publicació: Journal Publications

  • Paraules clau:

    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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