کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5288431 | 1385826 | 2005 | 4 صفحه PDF | دانلود رایگان |
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.
Journal: Tetrahedron Letters - Volume 46, Issue 18, 2 May 2005, Pages 3253-3256