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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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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. |
format | Online Article Text |
id | pubmed-9457760 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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