Synthesis of reactive trichloroacetimidates using polymer supported DBU catalysis

Abstract

Trichloroacetimidates are commonly synthesized to be used as alkylating or glycosylating reagents. They are synthesized from an alcohol and trichloroacetonitrile and DBU is the preferred base catalyst for this reaction. Here is presented a method, where commercially available solid supported DBU (PS-DBU) is used as the catalyst (3–8 mol%) resulting in a less discolored reaction and a simpler isolation of labile products by filtration and concentration, avoiding workup and chromatography. Small volatile trichloroacetimidates can hence be synthesized in an advantageous and economical way.