Issue 23, 2008
From the journal:

Organic & Biomolecular Chemistry

Stereoselective aziridination of cyclic allylic alcohols using chloramine-T†

Susannah C. Coote,a   Peter O'Brien*a  and  Adrian C. Whitwood‡a  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, York, UK
E-mail: paob1@york.ac.uk
Fax: +44 1904 432516
Tel: +44 1904 432535

Abstract

The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC6H4SO2NClNa, TsNClNa and t-BuSO2NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis-hydroxy aziridine, whilst complete cis-diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis-stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.

Graphical abstract: Stereoselective aziridination of cyclic allylic alcohols using chloramine-T

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Article information

DOI
https://doi.org/10.1039/B811137E
Article type
Paper
Submitted
01 Jul 2008
Accepted
26 Aug 2008
First published
08 Oct 2008

Org. Biomol. Chem., 2008,6, 4299-4314

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Stereoselective aziridination of cyclic allylic alcohols using chloramine-T

S. C. Coote, P. O'Brien and A. C. Whitwood, Org. Biomol. Chem., 2008, 6, 4299 DOI: 10.1039/B811137E

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