Nitrogen-Centered Radical-Mediated Cascade Amidoglycosylation of Glycals
Wenbin Shang, Chunyu Zhu, Fengyuan Peng, Zhiqiang Pan, Yuzhen Ding, Chengfeng Xia
Abstract
A nitrogen-centered radical-mediated strategy for preparing 1,2-trans-2-amino-2-deoxyglycosides in one step was established. The cascade amidoglycosylation was initiated by a benzenesulfonimide radical generated from NFSI under the catalytic reduction of TEMPO. The benzenesulfonimide radical was electrophilically added to the glycals, and then the resulting glycosidic radical was converted to oxocarbenium upon oxidation by TEMPO+, which enabled the following anomeric specific glycosylation.
Topics & Concepts
ChemistryAnomerOxocarbeniumGlycosidic bondGlycosylationCascadeCatalysisNitrogenOrganic chemistryCombinatorial chemistryNucleophileBiochemistryEnzymeChromatographyCarbohydrate Chemistry and SynthesisChemical Synthesis and AnalysisSulfur-Based Synthesis Techniques