Jianhui Huang, P. O’Brien
May 2, 2005
Citations
0
Influential Citations
7
Citations
Journal
ChemInform
Abstract
Abstract In a continuing study on the α-lithiation of N -tosyl aziridines, it is reported that ortho -lithiation of the N -tosyl group is occurring under typical α-lithiation conditions ( s -BuLi/PMDETA). Thus, a simple, two-step synthesis of N -2,4,6-triisopropylbenzenesulfonyl aziridines was optimised. The route involves epoxide ring opening using a sulfonamide, mesylation and base-mediated ring closure. The scope and limitations of this route were assessed and five new N -2,4,6-triisopropylbenzenesulfonyl aziridines were prepared in good yields. Since this method was unsuitable for the preparation of cyclooctene aziridine, an alternative two-step method was developed. This method involved aminobromination of cyclooctene using NBS/2,4,6-triisopropylbenzenesulfonamide.