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Issue 55, 2014
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Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates

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Abstract

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 SN2 (Rh2(OAc)4/PhI(OPiv)2) or SN2′ (Rh2(OPiv)4/PhI(OAc)2) opening. The scope and limitations of this tandem process are described.

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

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Publication details

The article was received on 19 Feb 2014, accepted on 16 May 2014 and first published on 16 May 2014


Article type: Communication
DOI: 10.1039/C4CC01312C
Citation: Chem. Commun., 2014,50, 7344-7347
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    Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates

    J. Guasch, Y. Díaz, M. I. Matheu and S. Castillón, Chem. Commun., 2014, 50, 7344
    DOI: 10.1039/C4CC01312C

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