1,2-trans-Stereoselective Synthesis of C-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 C-glycosides of 2-deoxy-2-amino sugars has been developed. Complementary to previous strategies, the reaction is 1,2-trans-stereoselective and could use aryl alkenes as substrates. The late-stage functionalization and density functional theory calculations are reported.