Bifunctional Cinchona Alkaloid/Thiourea Catalyzes Direct and Enantioselective Vinylogous Michael Addition of 3-Alkylidene Oxindoles to Nitroolefins

Bifunctional Cinchona Alkaloid/Thiourea Catalyzes Direct and Enantioselective Vinylogous Michael Addition of 3-Alkylidene Oxindoles to Nitroolefins

Vinylogy: Advances in asymmetric catalysis using the bifunctional cinchona alkaloid/thioureas enabled an umpolung of the classical Cβ reactivity of 3‐alkylidene oxindoles, thus allowing the development of the first and sole example of a direct, organocatalytic asymmetric vinylogous Michael (AVM) rea...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2012-06, Vol.51 (25), p.6200-6204
Hauptverfasser: Curti, Claudio, Rassu, Gloria, Zambrano, Vincenzo, Pinna, Luigi, Pelosi, Giorgio, Sartori, Andrea, Battistini, Lucia, Zanardi, Franca, Casiraghi, Giovanni
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids
Alkylation
asymmetric synthesis
Asymmetry
Catalysis
Cinchona Alkaloids - chemistry
heterocycles
Indoles - chemistry
Michael reaction
Molecular Structure
organocatalysis
Sole
Stereoisomerism
Thiourea - chemistry
Thioureas
umpolung
Vinyl Compounds - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Vinylogy: Advances in asymmetric catalysis using the bifunctional cinchona alkaloid/thioureas enabled an umpolung of the classical Cβ reactivity of 3‐alkylidene oxindoles, thus allowing the development of the first and sole example of a direct, organocatalytic asymmetric vinylogous Michael (AVM) reaction with nitroolefins.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201202027