García Castillo, Jesús María

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https://academica-e.unavarra.es/handle/2454/49075

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García Castillo

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Jesús María

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Ciencias

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InaMat2. Instituto de Investigación en Materiales Avanzados y Matemáticas

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0000-0001-6632-097X

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88464

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573

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End date: 2023 × Start date: 2020 ×

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    PublicationOpen Access
    Organocatalytic Michael addition of unactivated a-branched nitroalkanes to afford optically active tertiary nitrocompounds
    (American Chemical Society, 2023) Lorea Revilla, Beñat; García-Urricelqui, Ane; Odriozola Ibarguren, José Manuel; Razkin Lizarraga, Jesús; Espinal Viguri, Maialen; Oiarbide, Mikel; Mielgo, Antonia; García Castillo, Jesús María; Palomo, Claudio; Ciencias; Zientziak; Institute for Advanced Materials and Mathematics - INAMAT2; Gobierno de Navarra / Nafarroako Gobernua; Universidad Pública de Navarra / Nafarroako Unibertsitate Publikoa, PJUPNA18- 2022
    The direct, asymmetric conjugate addition of unactivated ¿-branched nitroalkanes is developed based on the combined use of chiral amine/ureidoaminal bifunctional catalysts and a tunable acrylate template to provide tertiary nitrocompounds in 55¿80% isolated yields and high enantioselectivity (e.r. up to 96:4). Elaboration of the ketol moiety in thus obtained adducts allows a fast entry to not only carboxylic and aldehyde derivatives but also nitrile compounds and enantioenriched 5,5-disubstituted ¿-lactams.
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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.