Issue 19, 2007
From the journal:

Chemical Communications

Stereospecific aziridination of olefinsviaelectrophile-induced cyclization of γ,δ-unsaturated imines and subsequent hydrolytic rearrangement†

Matthias D'hooghe,a   Mark Boelens,a   Johan Piqueura  and  Norbert De Kimpe*a  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium
E-mail: norbert.dekimpe@UGent.be
Fax: +32 9 264 6243
Tel: +32 9 264 5951

Abstract

The olefinic bond of γ,δ-unsaturated aldehydes underwent a net aziridination through electrophile-induced cyclization and subsequent rearrangement of the resulting cyclic iminium salts: this methodology allows the stereospecific introduction of aziridine moieties into cyclic systems.

Graphical abstract: Stereospecific aziridination of olefinsviaelectrophile-induced cyclization of γ,δ-unsaturated imines and subsequent hydrolytic rearrangement

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Article information

DOI
https://doi.org/10.1039/B703147E
Article type
Communication
Submitted
01 Mar 2007
Accepted
27 Mar 2007
First published
13 Apr 2007

Chem. Commun., 2007, 1927-1929

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Stereospecific aziridination of olefinsviaelectrophile-induced cyclization of γ,δ-unsaturated imines and subsequent hydrolytic rearrangement

M. D'hooghe, M. Boelens, J. Piqueur and N. D. Kimpe, Chem. Commun., 2007, 1927 DOI: 10.1039/B703147E

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