Nitrogen-Centered Radical Mediated Anomeric Specific Cascade Amidoglycosylation of Glycals

Abstract

A nitrogen-centered radical-mediated strategy to prepare 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 electrophilic added to the glycals, then the resulted glycosidic radical was converted to oxocarbenium upon oxidation by TEMPO+, and enabled the following anomeric specific glycosylation.