Nitrogen-Centered Radical-Mediated Cascade Amidoglycosylation of Glycals.


Shang W(1), Zhu C(1), Peng F(1), Pan Z(1), Ding Y(1), Xia C(1).
Author information:
(1)Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.


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.