Stereoselective aziridination of cyclic allylic alcohols using chloramine-T

Coote, Susannah C. and O'Brien, Peter and Whitwood, Adrian C. (2008) Stereoselective aziridination of cyclic allylic alcohols using chloramine-T. Organic and Biomolecular Chemistry, 6 (23). pp. 4299-4314. ISSN 1477-0520

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Abstract

The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC(6)H(4)SO(2)NClNa, TsNClNa and t-BuSO(2)NClNa, 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.

Item Type:
Journal Article
Journal or Publication Title:
Organic and Biomolecular Chemistry
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600/1606
Subjects:
ID Code:
72302
Deposited By:
Deposited On:
05 Jan 2015 11:20
Refereed?:
Yes
Published?:
Published
Last Modified:
01 Jan 2020 09:05