| Title |
Copper-catalyzed S-arylation of furanose-fused oxazolidine-2-thiones / |
| Authors |
Kederienė, Vilija ; Rousseau, Jolanta ; Schuler, Marie ; Šačkus, Algirdas ; Tatibouët, Arnaud |
| DOI |
10.3390/molecules27175597 |
| Full Text |
|
| Is Part of |
Molecules.. Basel : MDPI. 2022, vol. 27, iss. 17, art. no. 5597, p. 1-17.. ISSN 1420-3049 |
| Keywords [eng] |
C-S bond formation ; S-arylation ; carbohydrates ; copper catalysis ; oxazolidine-2-thione |
| Abstract [eng] |
The 1,3-oxazolidine-2-thiones (OZTs) are important chiral molecules, especially in asymmetric synthesis. These compounds serve as important active units in biologically active compounds. Herein, carbohydrate anchored OZTs were explored to develop a copper-catalyzed C-S bond formation with aryl iodides. Chemoselective S-arylation was observed, with copper iodide and dimethylethylenediamine (DMEDA) as the best ligand in dioxane at 60-90 °C. The corresponding chiral oxazolines were obtained in reasonable to good yields under relatively mild reaction conditions. This approach is cheap, as using one of the cheapest transition metals, a simple protocol and various functional group tolerance make it a valuable strategy for getting S-substituted furanose-fused OZT. The structures of the novel carbohydrates were confirmed by NMR spectroscopy and an HRMS analysis. |
| Published |
Basel : MDPI |
| Type |
Journal article |
| Language |
English |
| Publication date |
2022 |
| CC license |
|
