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    Enantioselective addition of alkynyl ketones to nitroolefins assisted by Brønsted base/H-bonding catalysis

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    2019060092_Campano_EnantioselectiveAddition.pdf (1.226Mb)
    Date
    2019
    Author
    Campano, Teresa E. 
    Iriarte, Igor 
    Olaizola, Olatz 
    Etxabe, Julen 
    Mielgo, Antonia 
    Ganboa, Iñaki 
    Odriozola Ibarguren, José Manuel Upna Orcid
    García Castillo, Jesús María Upna Orcid
    Oiarbide, Mikel 
    Palomo, Claudio 
    Version
    Acceso abierto / Sarbide irekia
    Type
    Artículo / Artikulua
    Version
    Versión aceptada / Onetsi den bertsioa
    Project Identifier
    ES/1PE/CTQ2016-78487 
    Impact
     
     
     
    10.1002/chem.201805542
     
     
     
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    Abstract
    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 optic ... [++]
    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. [--]
    Subject
    Alkynyl ketones, Asymmetric catalysis, Brønsted bases, Michael reaction, Organocatalysis
     
    Publisher
    Wiley
    Published in
    Chemistry: A European Journal, 2019, 25 (17), 4390-4397
    Departament
    Universidad Pública de Navarra. Departamento de Ciencias / Nafarroako Unibertsitate Publikoa. Zientziak Saila / Universidad Pública de Navarra / Nafarroako Unibertsitate Publikoa. INAMAT2 - Institute for Advanced Materials and Mathematics
     
    Publisher version
    https://doi.org/10.1002/chem.201805542
    URI
    https://hdl.handle.net/2454/35938
    Sponsorship
    Financial support was provided by the University of the Basque Country UPV/EHU (UFI QOSYC 11/22), Basque Government (BG Grant No IT-628-13), and Ministerio de Economía y Competitividad (MINECO, Grant CTQ2016-78487-C2), Spain, T.C. thanks MINECO, and I.I. and O.O. thank BG for fellowships.
    Appears in Collections
    • Artículos de revista - Aldizkari artikuluak [4586]
    • Artículos de revista INAMAT2 - INAMAT2 aldizkari artikuluak [279]
    • Artículos de revista DCIE - ZIES Aldizkari artikuluak [198]
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