Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds

Martí Fernández, Magda Parera, Teodor Parella, Agustí Lledó, Jean Le Bras, Jacques Muzart, Anna Pla-Quintana, Anna Roglans

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    4 Citations (Scopus)

    Abstract

    © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yields.
    Original languageEnglish
    Pages (from-to)1848-1853
    JournalAdvanced Synthesis and Catalysis
    Volume358
    Issue number11
    DOIs
    Publication statusPublished - 1 Jan 2016

    Keywords

    • cycloaddition
    • diastereoselectivity
    • kinetic resolution
    • Morita-Baylis-Hillman adducts
    • rhodium

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