Nitrogen-Centered Radical-Mediated Cascade Amidoglycosylation of Glycals
| Autor: | Chunyu Zhu, Zhiqiang Pan, Yuzhen Ding, Fengyuan Peng, Wenbin Shang, Chengfeng Xia |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Anomer Glycosylation Molecular Structure 010405 organic chemistry Chemistry Nitrogen Organic Chemistry Oxocarbenium Selective catalytic reduction Glycosidic bond 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Cascade Molecule Glycosides Physical and Theoretical Chemistry Oxidation-Reduction |
| Zdroj: | Organic letters. 23(4) |
| ISSN: | 1523-7052 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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