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Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones

Abstract : 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.
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https://hal-univ-artois.archives-ouvertes.fr/hal-03773596
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Submitted on : Friday, September 9, 2022 - 12:24:46 PM
Last modification on : Tuesday, September 27, 2022 - 4:32:21 AM

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Vilija Kederienė, Jolanta Rousseau, Marie Schuler, Algirdas Šačkus, Arnaud Tatibouët. Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones. Molecules, MDPI, 2022, 27 (17), pp.5597. ⟨10.3390/molecules27175597⟩. ⟨hal-03773596⟩

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