作者:Jianhui Huang、Stephen P. Moore、Peter O'Brien、Adrian C. Whitwood、John Gilday
DOI:10.1039/b815957b
日期:——
A detailed study on the lithiation-electrophilic trapping of N-sulfonyl ethylene aziridines is described. The optimum results required use of a N-2,4,6-tri-iso-propylbenzenesulfonyl activating group and lithiation using 3 equiv. of s-BuLi–PMDETA for 1 minute before addition of the electrophile. In situ trapping with Me3SiCl was also successful. Electrophilic trapping with aldehydes provided a stereoselective
描述了对N-磺酰基亚乙基氮丙啶的锂化-亲电捕集的详细研究。最佳结果所需使用的Ñ -2,4,6-三异-propylbenzenesulfonyl使用3当量活化基团和锂化。的s- BuLi–PMDETA在加入亲电试剂之前先保持1分钟。用Me 3 SiCl原位捕获也很成功。醛的亲电捕集为合成-羟基氮丙啶提供了立体选择途径。或者,可以使用NaBH 4 -CeCl 3将酮氮丙啶立体选择性地还原为顺羟基氮丙啶。通过X射线晶体学明确地确定了两个羟基氮丙啶中的相对立体化学。