DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones

We examined the catalytic enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones 1 with N-fluorobenzenesulfonimide (NFSI) by DBFOX-Ph/metal complexes under a variety of conditions. After optimization of the metal salts, solvents and additives, we found that the fluoro-2-thiazolidinones...

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Detalles Bibliográficos
Autores principales: Ishimaru, Takehisa, Shibata, Norio, Reddy, Dhande Sudhakar, Horikawa, Takao, Nakamura, Shuichi, Toru, Takeshi
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Preliminary Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486487/
https://www.ncbi.nlm.nih.gov/pubmed/18941488
http://dx.doi.org/10.3762/bjoc.4.16
Descripción
Sumario:We examined the catalytic enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones 1 with N-fluorobenzenesulfonimide (NFSI) by DBFOX-Ph/metal complexes under a variety of conditions. After optimization of the metal salts, solvents and additives, we found that the fluoro-2-thiazolidinones 2 were obtained in good to high yields with moderate to good enantioselectivities (up to 78% ee) when the reaction was carried out in the presence of DBFOX-Ph (11 mol%), Ni(ClO(4))(2)·6H(2)O (10 mol%) and 2,6-lutidine (0 or 1.0 equiv) in CH(2)Cl(2).

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