Synthesis of Sulfonylated Cinchona Alkaloids via Zinc-Mediated Sulfonylation of the N-Oxides of the Quinoline Groups
| Autor: | Fu-She Han, Jie Zhou, Cheng-Yu Gu |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Synthesis. 54:4810-4817 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/a-1900-0293 |
| Popis: | A general and practical method for the synthesis of sulfonylated cinchona alkaloids is presented. The reactions are carried out via Zn-mediated nucleophilic aromatic substitution of the N-oxides of the quinoline core in cinchona alkaloids with a range of sulfonyl chlorides. By careful optimization of the reaction parameters and the procedure, both aromatic and aliphatic sulfonyl chlorides react efficiently with the N-oxides to afford the corresponding sulfonylated products in high yields. In addition, the reaction can be reliably scaled up to gram level. As a result, this method provides a practical route for the synthesis of new cinchona alkaloid derivatives that might be potentially useful compounds, particularly in asymmetric catalysis. |
| Databáze: | OpenAIRE |
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