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    Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/6089

    Título
    Aldol–Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivatives
    Autor
    Sedano Labrador, CarlosUBU authority Orcid
    Virumbrales Ortiz, CintiaUBU authority Orcid
    Suarez Pantiga, SamuelUBU authority Orcid
    Sanz Díez, RobertoUBU authority Orcid
    Publicado en
    Synthesis. 2021, V. 53, n. 20, p. 3725-3734
    Editorial
    Thieme
    Fecha de publicación
    2021-10
    ISSN
    0039-7881
    DOI
    10.1055/a-1509-5655
    Abstract
    α-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol–Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary stereocenter is attributed to stereoelectronic effects in the Evans intermediate. This methodology allows overcoming some limitations of our previously reported strategy, based on the reaction of α-lithiobenzyl ethers with esters and paraformaldehyde, broadening the scope of the obtained polyols. Synthetic applications of this process include the preparation of a new dilignol model and some functionalized oxetanes.
    Palabras clave
    aldol–Tishchenko reaction
    enolates
    α-oxy ketones
    polyol derivatives
    diastereoselectivity
    oxetanes
    Materia
    Química orgánica
    Chemistry, Organic
    URI
    http://hdl.handle.net/10259/6089
    Versión del editor
    https://doi.org/10.1055/a-1509-5655
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    • Artículos SINTORG
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