Issue 55, 2014
From the journal:

Chemical Communications

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

Joan Guasch,a   Yolanda Díaz,a   M. Isabel Matheu*a  and  Sergio Castillón*a  

* Corresponding authors

a Department of Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/Marcel·lí Domingo s/n, 43007 Tarragona, Spain
E-mail: sergio.castillon@urv.cat, maribel.matheu@urv.cat

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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Article information

DOI
https://doi.org/10.1039/C4CC01312C
Article type
Communication
Submitted
19 Feb 2014
Accepted
16 May 2014
First published
16 May 2014

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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