1,2-<i>trans</i>-Stereoselective Synthesis of <i>C</i>-Glycosides of 2-Deoxy-2-amino-sugars Involving Glycosyl Radicals

Abstract

We report for the first time that the imidate radical can be efficiently added to glycals to generate glycosyl radicals, based on which a general, toxic-reagent-free synthesis of <i>C</i>-glycosides of 2-deoxy-2-amino sugars has been developed. Complementary to previous strategies, the reaction is 1,2-<i>trans</i>-stereoselective and could use aryl alkenes as substrates. The late-stage functionalization and density functional theory calculations are reported.