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

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 iodid...

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Autores principales: Kederienė, Vilija, Rousseau, Jolanta, Schuler, Marie, Šačkus, Algirdas, Tatibouët, Arnaud
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457760/
https://www.ncbi.nlm.nih.gov/pubmed/36080364
http://dx.doi.org/10.3390/molecules27175597
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author Kederienė, Vilija
Rousseau, Jolanta
Schuler, Marie
Šačkus, Algirdas
Tatibouët, Arnaud
author_facet Kederienė, Vilija
Rousseau, Jolanta
Schuler, Marie
Šačkus, Algirdas
Tatibouët, Arnaud
author_sort Kederienė, Vilija
collection PubMed
description 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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spelling pubmed-94577602022-09-09 Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones Kederienė, Vilija Rousseau, Jolanta Schuler, Marie Šačkus, Algirdas Tatibouët, Arnaud Molecules Article 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. MDPI 2022-08-30 /pmc/articles/PMC9457760/ /pubmed/36080364 http://dx.doi.org/10.3390/molecules27175597 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kederienė, Vilija
Rousseau, Jolanta
Schuler, Marie
Šačkus, Algirdas
Tatibouët, Arnaud
Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones
title Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones
title_full Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones
title_fullStr Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones
title_full_unstemmed Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones
title_short Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones
title_sort copper-catalyzed s-arylation of furanose-fused oxazolidine-2-thiones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457760/
https://www.ncbi.nlm.nih.gov/pubmed/36080364
http://dx.doi.org/10.3390/molecules27175597
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