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

Vilija Kederienė (1) , Jolanta Rousseau (2) , Marie Schuler (3) , Algirdas Šačkus (1) , Arnaud Tatibouët (3)

1 KTU - Kaunas University of Technology
2 UCCS Équipe Catalyse Supramoléculaire
3 ICOA - Institut de Chimie Organique et Analytique

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.

Mots clés: copper catalysis; carbohydrates; S-arylation; C-S bond formation; oxazolidine-2-thione

Domaines: Catalyse; Chimie

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