Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates

Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates

The reaction of dienyl carbamates with PhI(OR)2 in the presence of rhodium catalysts affords vinyl aziridines which are in situ regio- and stereoselectively opened to afford oxyamination products resulting from a selective S(N)2 (Rh2(OAc)4/PhI(OPiv)2) or S(N)2' (Rh2(OPiv)4/PhI(OAc)2) opening. T...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical communications (Cambridge, England) England), 2014-01, Vol.50 (55), p.7344-7347
Hauptverfasser: Guasch, Joan, Díaz, Yolanda, Matheu, M Isabel, Castillón, Sergio
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The reaction of dienyl carbamates with PhI(OR)2 in the presence of rhodium catalysts affords vinyl aziridines which are in situ regio- and stereoselectively opened to afford oxyamination products resulting from a selective S(N)2 (Rh2(OAc)4/PhI(OPiv)2) or S(N)2' (Rh2(OPiv)4/PhI(OAc)2) opening. The scope and limitations of this tandem process are described.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc01312c