title: Stereoselective aziridination of cyclic allylic alcohols using chloramine-T.
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.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, UKYO10 5DD.
authors.forename: Susannah C
authors.initials: SC
authors.lastname: Coote
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.forename: Adrian C
authors.initials: AC
authors.lastname: Whitwood