1,2-<i>trans</i>-Stereoselective Synthesis of <i>C</i>-Glycosides of 2-Deoxy-2-amino-sugars Involving Glycosyl Radicals
Wenze Shi, Hai Li, Gui-Cai Mu, Ji-Liang Lu, Yuan‐Hong Tu, Xiang‐Guo Hu
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.
Topics & Concepts
ChemistryStereoselectivityGlycosylRadicalReagentArylGlycosideCombinatorial chemistryOrganic chemistryStereochemistryCatalysisAlkylCarbohydrate Chemistry and SynthesisRadical Photochemical ReactionsSulfur-Based Synthesis Techniques