Issue 23, 2011
From the journal:

Chemical Communications

Gold(i)-catalyzed rearrangement of aryl alkynylaziridines to spiro[isochroman-4,2′-pyrrolines]†

Nicolas Kern,a   Aurélien Blanc,*a   Jean-Marc Weibela  and  Patrick Pale*a  

* Corresponding authors

a Laboratoire de Synthèse et Réactivité Organiques, associé au CNRS, Institut de Chimie, Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg, France
E-mail: ablanc@unistra.fr, ppale@unistra.fr
Fax: +33 368851517
Tel: +33 368851517

Abstract

Alkynylaziridines carrying an aryl group could be efficiently converted to spiro[isochroman-4,2′-pyrrolines] with gold salts as catalysts. This new rearrangement involved a Friedel–Crafts type intramolecular reaction followed by cyclization of the aminoallene intermediate, both initiated by the dual σ and π Lewis acidities of gold.

Graphical abstract: Gold(i)-catalyzed rearrangement of aryl alkynylaziridines to spiro[isochroman-4,2′-pyrrolines]

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Article information

DOI
https://doi.org/10.1039/C1CC11351H
Article type
Communication
Submitted
08 Mar 2011
Accepted
11 Apr 2011
First published
05 May 2011

Chem. Commun., 2011,47, 6665-6667

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Gold(I)-catalyzed rearrangement of aryl alkynylaziridines to spiro[isochroman-4,2′-pyrrolines]

N. Kern, A. Blanc, J. Weibel and P. Pale, Chem. Commun., 2011, 47, 6665 DOI: 10.1039/C1CC11351H

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