Enantioselective Synthesis of Spirothiazolones via Cooperative Catalysis

Cooperative amino‐ and palladium catalysis utilizing heterocyclic systems containing strongly coordinating and adsorptive sulfur atom remains an underdeveloped area. Herein, we describe an enantioselective cyclization of enals with thiazole derivatives catalyzed with the combination of achiral Pd(0)...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Advanced synthesis & catalysis 2021-09, Vol.363 (18), p.4349-4353
Hauptverfasser: Franc, Michael, Císařová, Ivana, Veselý, Jan
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Cooperative amino‐ and palladium catalysis utilizing heterocyclic systems containing strongly coordinating and adsorptive sulfur atom remains an underdeveloped area. Herein, we describe an enantioselective cyclization of enals with thiazole derivatives catalyzed with the combination of achiral Pd(0) complexes and chiral secondary amines. Chiral spirocyclic thiazolones were produced in yields ranging from 41% to 98% with stereoselectivities (from 5:1 to 12:1 dr, and 95–99% ee). Moreover, the developed strategy allows access to highly substituted chiral cyclopentane derivatives by additional transformations of spirocyclic thiazolones.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100571