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    Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/5535

    Título
    Merging α-Lithiation and Aldol-Tishchenko Reaction to Construct Polyols from Benzyl Ethers
    Autor
    Sedano Labrador, CarlosUBU authority Orcid
    Velasco, Rocío
    Suárez Pantiga, SamuelUBU authority Orcid
    Sanz Díez, RobertoUBU authority Orcid
    Publicado en
    Organic Letters. 2020, V. 22, n. 20, p. 8070–8075
    Editorial
    American Chemical Society
    Fecha de publicación
    2020-10
    ISSN
    1523-7060
    DOI
    10.1021/acs.orglett.0c03014
    Abstract
    α-Lithiobenzyl ethers, generated by selective α-lithiation, undergo an aldol-Tishchenko reaction upon treatment with carboxylic esters and paraformaldehyde. The reaction of the organolithium with the carboxylate generates an intermediate enolate that, after formaldehyde addition, affords 1,2,3-triol derivatives in a straightforward and one-pot manner. These products are obtained as single diastereoisomers bearing a quaternary stereocenter. The complete diastereocontrol of the aldol-Tishchenko process is attributed to stereoelectronic preferences in the transition state.
    Palabras clave
    Reaction products
    Aldehydes
    Ethers
    Pharmaceuticals
    Aldol reactions
    Materia
    Química orgánica
    Chemistry, Organic
    URI
    http://hdl.handle.net/10259/5535
    Versión del editor
    https://doi.org/10.1021/acs.orglett.0c03014
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    • Artículos SINTORG
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