Model synthesis of six-membered carbocyclic spironucleosides

0351445 - ÚOCHB 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 MŠMT 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