Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p -toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical communications (Cambridge, England) England), 2018-03, Vol.54 (25), p.3166-3169
Hauptverfasser: Niemi, Teemu, Fernández, Israel, Steadman, Bethany, Mannisto, Jere K, Repo, Timo
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p -toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a S N 2-type reaction mechanism with high regio-, chemo-, and stereoselectivity. Selective, straightforward, and efficient synthesis of cyclic carbamates from CO 2 and amino alcohols.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc00636a