Stereospecific cyclodehydration of 1,4-sulfanylalcohols to thiolanes: mechanistic insights
作者:Jean-Jacques Filippi、Elisabet Duñach、Xavier Fernandez、Uwe J. Meierhenrich
DOI:10.1016/j.tet.2008.07.088
日期:2008.10
A series of thiolanes were prepared by cyclodehydration of sulfanylalcohols in the presence of catalytic amounts of p-toluenesulfonic acid or by using K10 clay. The sulfur heterocycles were synthesised in good to excellent yields using either a conventional Dean–Stark method or microwave irradiation under solvent-free conditions. The reaction could be performed regio- and stereoselectively and its
在催化量的对甲苯磺酸存在下,通过环硫烷硫醇的脱水反应或使用K10粘土制备了一系列硫杂环戊烷。使用常规的迪安-斯达克方法或在无溶剂条件下用微波辐照,可以很好地合成优良的硫杂环化合物。该反应可以区域和立体选择性地进行,并且通过对映体和非对映体富集的底物研究了其机理。相较于以前的研究,我们的结果与分子内的一致ň 2型机构作为一般的途径。