Issue 20, 2011
From the journal:

Organic & Biomolecular Chemistry

Claisen rearrangements of equilibrating allylic azides†

Donald Craig,*a   John W. Harvey,b   Alexander G. O'Briena  and  Andrew J. P. Whitec  

* Corresponding authors

a Department of Chemistry, Imperial College London, South Kensington Campus, London, UK
E-mail: d.craig@imperial.ac.uk
Fax: +44 (0)20 7594 5804
Tel: +44 (0)20 7594 5771

b Discovery Chemistry, Pfizer Global Research and Development, Ramsgate Road, Sandwich, Kent, UK

c Chemical Crystallography Laboratory, Imperial College London, South Kensington Campus, London, UK

Abstract

Equilibrating mixtures of allylic azide-containing allylic alcohols or allylic 2-tolylsulfonylacetic esters undergo Johnson–Claisen or Ireland–Claisen rearrangement reactions to give unsaturated γ-azidoesters and -acids, respectively. Decarboxylation of the acids under basic conditions gives azidosulfones, with moderate to high diastereoselectivity.

Graphical abstract: Claisen rearrangements of equilibrating allylic azides

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Article information

DOI
https://doi.org/10.1039/C1OB05972F
Article type
Paper
Submitted
13 Apr 2011
Accepted
30 Jun 2011
First published
30 Aug 2011

Org. Biomol. Chem., 2011,9, 7057-7061

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Claisen rearrangements of equilibrating allylic azides

D. Craig, J. W. Harvey, A. G. O'Brien and A. J. P. White, Org. Biomol. Chem., 2011, 9, 7057 DOI: 10.1039/C1OB05972F

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