Odriozola Ibarguren, José Manuel

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https://academica-e.unavarra.es/handle/2454/49664

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Odriozola Ibarguren

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José Manuel

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Ciencias

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InaMat2. Instituto de Investigación en Materiales Avanzados y Matemáticas

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0000-0002-0063-8325

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88548

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2204

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Subject: Acrolein ×

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    PublicationOpen Access
    Development of an α′-hydroxy enone for the aminocatalytic asymmetric formal conjugate addition of aldehydes to acrylates, vinyl ketones and acrolein
    (Royal Society of Chemistry, 2023) Odriozola Ibarguren, José Manuel; Razkin Lizarraga, Jesús; Lorea Revilla, Beñat; Mielgo, Antonia; García Castillo, Jesús María; Oiarbide, Mikel; Palomo, Claudio; Ciencias; Zientziak; Institute for Advanced Materials and Mathematics - INAMAT2
    Aminocatalytic asymmetric conjugate addition of aldehydes to Michael acceptors is a well established C-C bond forming methodology. However, various acrylic-type acceptors, including acrylic acid derivatives and acrolein, remain reluctant. Here we demonstrate that the internal H-bonding self-activation in α'-hydroxy enones allows them to react smoothly with enolizable aldehydes using commercially available aminocatalysts to afford adducts in good yields and high enantioselectivity. Straightforward conversion of the ketol moiety of these adducts into aldehyde, ketone and carboxylic acid functionalities offers an indirect, unified entry to products derived from acrolein, alkyl-vinyl ketones and acrylates, respectively.