A Copper Catalyst with a Cinchona-Alkaloid-Based Sulfonamide Ligand for Asymmetric Radical Oxytrifluoromethylation of Alkenyl Oximes
| Autor: | Xin-Yuan Liu, Qiang-Shuai Gu, Xiao-Yang Dong, Xi-Tao Li, Xiang Meng |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
biology Chemistry 010405 organic chemistry Enantioselective synthesis Rational design Cinchona General Chemistry General Medicine biology.organism_classification Oxime 010402 general chemistry Combinatorial chemistry 01 natural sciences Catalysis Stereocenter Sulfonamide 0104 chemical sciences chemistry.chemical_compound Reagent Alkyl |
| Zdroj: | Angewandte Chemie (International ed. in English). 57(26) |
| ISSN: | 1521-3773 |
| Popis: | A copper-catalyzed asymmetric radical oxytrifluoromethylation of alkenyl oxime and Togni's reagent has been successfully developed, thereby providing straightforward access to CF3 -containing isoxazolines bearing α-tertiary stereocenters with excellent yield and enantioselectivity. The key to success is the rational design of cinchona-alkaloid-based sulfonamides as neutral/anionic hybrid ligands to effectively control the stereochemistry in copper-catalyzed reactions involving free alkyl radical species. The utility of this method is illustrated by efficient transformation of the products into useful chiral CF3 -containing 1,3-aminoalcohols. |
| Databáze: | OpenAIRE |
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