A New Synthesis of trans-2,3-Diaryloxiranes and 2-(1H-Benzo[d][1,2,3]-[nl]triazol-1-yl)-1-arylethanols via the Reactions of 1-Benzyl-3-methylbenzo-[nl]triazolium Ylide with Aryl Aldehydes
作者:Xiaohui Xiao、Daqin Lin、Shuitian Tong、Hailan Mo
DOI:10.1055/s-0031-1289555
日期:2011.12
1-Benzyl-3-methylbenzotriazolium ylide was formed by the reaction of 1-benzyl-3-methylbenzotriazolium iodide with t-BuOK. Subsequently it reacted with various aryl aldehydes to give the corresponding trans-2,3-diaryloxiranes and 2-(1H-benzo-[d][1,2,3]triazol-1-yl)-1-arylethanols in moderate to high yields.
A new synthetic approach toward difunctionalization of alkenes has been developed under metal-free conditions. Various carboxylic acids and amines could react smoothly with alkenes to give dioxygenation and oxyamidation products, respectively. This organocatalytic process delivers 2-hydroxy alcohols directly from simple alkenes with high levels of region control.