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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2018 - 20192
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Subject: Organocatalysis ×

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Now showing 1 - 2 of 2
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    PublicationOpen Access
    α-Hydroxy ketones as masked ester donors in Brønsted base catalyzed conjugate additions to nitroalkenes
    (Wiley, 2018) Olaizola, Iurre; Campano, Teresa E.; Iriarte, Igor; Vera, Silvia; Mielgo, Antonia; García Castillo, Jesús María; Odriozola Ibarguren, José Manuel; Oiarbide, Mikel; Palomo, Claudio; Institute for Advanced Materials and Mathematics - INAMAT2; Química Aplicada; Kimika Aplikatua
    The catalyst-controlled enantioselective direct addition reaction of enolizable esters and related carboxylic acid derivatives to p electrophiles remains a difficult synthetic transformation. In this study, the suitability of a-hydroxy ketones as ester equivalents capable of being activated by bifunctional Brønsted base catalysts in the context of conjugate addition reactions to nitroolefins is demonstrated. The scope of the reaction, which affords the corresponding Michael adducts with very high stereoselectivity (diastereomeric ratio (d.r.) +95:5, up to 99% enantiomeric excess (ee)), and its limitations are explored, as is the aftermath elaboration of adducts into densely functionalized enantioenriched products.
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    PublicationOpen Access
    Enantioselective addition of alkynyl ketones to nitroolefins assisted by Brønsted base/H-bonding catalysis
    (Wiley, 2019) Campano, Teresa E.; Iriarte, Igor; Olaizola, Olatz; Etxabe, Julen; Mielgo, Antonia; Ganboa, Iñaki; Odriozola Ibarguren, José Manuel; García Castillo, Jesús María; Oiarbide, Mikel; Palomo, Claudio; Zientziak; Institute for Advanced Materials and Mathematics - INAMAT2; Ciencias
    Various sets of enolizable alkynyl ketones (including methyl ynones with α-aryl, α-alkenyl, and α-alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Brønsted base/H-bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly diastereo- and enantioselective fashion. Further transformation of the obtained adducts into optically active acyclic and polycyclic molecules, including some with intricate carbon skeletons, was also demonstrated.