Copper-catalyzed S-arylation of Furanose-Fused ...
Document type :
Article dans une revue scientifique: Article original
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Title :
Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones
Author(s) :
Kederienė, V. [Auteur]
Kaunas University of Technology [KTU]
Rousseau, Jolanta [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Schuler, M. [Auteur]
Institut de Chimie Organique et Analytique [ICOA]
Šačkus, A. [Auteur]
Kaunas University of Technology [KTU]
Tatibouët, A. [Auteur]
Institut de Chimie Organique et Analytique [ICOA]
Kaunas University of Technology [KTU]
Rousseau, Jolanta [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Schuler, M. [Auteur]
Institut de Chimie Organique et Analytique [ICOA]
Šačkus, A. [Auteur]
Kaunas University of Technology [KTU]
Tatibouët, A. [Auteur]
Institut de Chimie Organique et Analytique [ICOA]
Journal title :
Molecules
Volume number :
27
Pages :
5597
Publication date :
2022-09-13
ISSN :
1420-3049
Keyword(s) :
oxazolidine-2-thione
C-S bond formation
S-arylation
carbohydrates
copper catalysis
C-S bond formation
S-arylation
carbohydrates
copper catalysis
HAL domain(s) :
Chimie/Catalyse
English abstract : [en]
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 ...
Show more >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.Show less >
Show more >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.Show less >
Language :
Anglais
Audience :
Internationale
Popular science :
Non
Administrative institution(s) :
Université de Lille
CNRS
Centrale Lille
ENSCL
Univ. Artois
CNRS
Centrale Lille
ENSCL
Univ. Artois
Collections :
Research team(s) :
Catalyse et chimie supramoléculaire (CASU)
Submission date :
2023-05-30T15:12:12Z
2023-06-09T11:54:47Z
2023-06-09T11:54:47Z
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