Articles producció científicaQuímica Física i Inorgànica

Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach

  • Dades identificatives

    Identificador:  imarina:9440136
    Handle: https://hdl.handle.net/20.500.11797/imarina9440136
    Autors:  Calow, Adam D J; Fernandez, Elena; Whiting, Andrew
    Resum:
    We report efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from alpha,beta-unsaturated aldehydes conducting five sequential one-pot steps (imine formation/copper mediated beta-borylation/transimination/reduction/oxidation) followed by the specific ether group formation which deliver the desired products (R)-fluoxetine in 45% yield (96% ee) and (S)-duloxetine in 47% yield (94% ee).

  • Altres:

    Autor segons l'article: Calow, Adam D J; Fernandez, Elena; Whiting, Andrew
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Fernández Gutiérrez, Maria Elena
    Paraules clau: Transformation; Tomoxetin; Synthesis of fluoxetine; Selective serotonin; Practical synthesis; One-pot; Hydrogenation; Gamma-amino alcohols; Enantioselective synthesis; Asymmetric aldol reaction; (r)-fluoxetine
    Resum: We report efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from alpha,beta-unsaturated aldehydes conducting five sequential one-pot steps (imine formation/copper mediated beta-borylation/transimination/reduction/oxidation) followed by the specific ether group formation which deliver the desired products (R)-fluoxetine in 45% yield (96% ee) and (S)-duloxetine in 47% yield (94% ee).
    Àrees temàtiques: Química; Physical and theoretical chemistry; Organic chemistry; Odontología; Medicina ii; Medicina i; Materiais; Interdisciplinar; General medicine; Farmacia; Ciências biológicas iii; 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: mariaelena.fernandez@urv.cat
    Data d'alta del registre: 2025-02-18
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://pubs.rsc.org/en/content/articlelanding/2014/ob/c4ob01142b/unauth
    Referència a l'article segons font original: Organic & Biomolecular Chemistry. 12 (32): 6121-6127
    Referència de l'ítem segons les normes APA: Calow, Adam D J; Fernandez, Elena; Whiting, Andrew (2014). Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach. Organic & Biomolecular Chemistry, 12(32), 6121-6127. DOI: 10.1039/c4ob01142b
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1039/c4ob01142b
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2014
    Tipus de publicació: Journal Publications

  • Paraules clau:

    Biochemistry,Chemistry, Organic,Organic Chemistry,Physical and Theoretical Chemistry
    Transformation
    Tomoxetin
    Synthesis of fluoxetine
    Selective serotonin
    Practical synthesis
    One-pot
    Hydrogenation
    Gamma-amino alcohols
    Enantioselective synthesis
    Asymmetric aldol reaction
    (r)-fluoxetine
    Química
    Physical and theoretical chemistry
    Organic chemistry
    Odontología
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    Farmacia
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry, organic
    Biotecnología
    Biodiversidade
    Biochemistry

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