Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids
| Autor: | Peng Ji, Wenbo Hu, Yongyi Wei, He Huang, Yueteng Zhang, Patrick A Mariano, Wei Wang |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Addition reaction 010405 organic chemistry Chemistry Radical Organic Chemistry Pentose 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Amino acid carbohydrates (lipids) chemistry.chemical_compound Nucleophile Electrophile lipids (amino acids peptides and proteins) Stereoselectivity Glycosyl Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 21(9) |
| ISSN: | 1523-7052 |
| Popis: | An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives. |
| Databáze: | OpenAIRE |
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