Počet záznamů: 1

Model synthesis of six-membered carbocyclic spironucleosides

  1. 1.
    0351445 - UOCHB-X 2011 RIV CZ eng J - Článek v odborném periodiku
    Nencka, Radim - Hřebabecký, Hubert - Dračínský, Martin
    Model synthesis of six-membered carbocyclic spironucleosides.
    Collection of Czechoslovak Chemical Communications. Roč. 75, č. 12 (2010), s. 1259-1272 ISSN 0010-0765
    Grant CEP: GA MŠk 1M0508
    Výzkumný záměr: CEZ:AV0Z40550506
    Klíčová slova: spironucleosides * carbocyclic * Bucherer-Bergs reaction * Michaels addition * tandem reaction
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 0.853, rok: 2010

    Model study focusing on the synthesis of carbocyclic spironucleosides is presented. Hydantoin base was built on the easily accessible ketone precursors by Bucherer–Bergs reaction. On saturated substrates the reaction proceeded smoothly. On α,β-unsaturated ketones, however, the Bucherer–Bergs reaction competed with Michael addition of cyanide ion. We showed that the equilibrium of the reaction could be significantly shifted depending on the applied reaction conditions. Significant diastereoselectivity was observed for tandem Michael addition/Bucherer–Bergs reaction.
    Trvalý link: http://hdl.handle.net/11104/0191199