Synthesis of Three New Bifunctional Glucose-Thiourea Organocatalysts and Their Application in Asymmetric Michael Addition

Three new glucose-based asymmetric bifunctional organocatalysts containing a 6-aminopyridyl or a 6-methylpyridyl or a cinchona unit were synthesized. Asymmetric Michael addition of pentane-2,4-dione to 0-nitrostyrene was catalyzed successfully by these catalysts. In case of the cinchona based glucos...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Studia Universitatis Babeș-Bolyai. Chemia 2017-03, Vol.62 (1), p.183-194
Hauptverfasser: Nagy, Sandor, Kozma, Petra, Kisszekelyi, Peter, Bezzegh, Dora, Huszthy, Peter, Kupai, Jozsef
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Three new glucose-based asymmetric bifunctional organocatalysts containing a 6-aminopyridyl or a 6-methylpyridyl or a cinchona unit were synthesized. Asymmetric Michael addition of pentane-2,4-dione to 0-nitrostyrene was catalyzed successfully by these catalysts. In case of the cinchona based glucose-thiourea derivate the S enantiomer of the corresponding Michael adduct was formed with moderate enantiomeric excess in three different solvents. Keywords: organocatalyst, carbohydrates, cinchona alkaloids, Michael addition, asymmetric syntheses
ISSN:1224-7154
2065-9520
DOI:10.24193/subbchem.2017.1.16