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...

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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
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creator Guasch, Joan
Díaz, Yolanda
Matheu, M Isabel
Castillón, Sergio
description 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.
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title Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates
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