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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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
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author Ishimaru, Takehisa
Shibata, Norio
Reddy, Dhande Sudhakar
Horikawa, Takao
Nakamura, Shuichi
Toru, Takeshi
author_facet Ishimaru, Takehisa
Shibata, Norio
Reddy, Dhande Sudhakar
Horikawa, Takao
Nakamura, Shuichi
Toru, Takeshi
author_sort Ishimaru, Takehisa
collection PubMed
description 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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spelling pubmed-24864872008-10-20 DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones Ishimaru, Takehisa Shibata, Norio Reddy, Dhande Sudhakar Horikawa, Takao Nakamura, Shuichi Toru, Takeshi Beilstein J Org Chem Preliminary Communication 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). Beilstein-Institut 2008-05-20 /pmc/articles/PMC2486487/ /pubmed/18941488 http://dx.doi.org/10.3762/bjoc.4.16 Text en Copyright © 2008, Ishimaru et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Preliminary Communication
Ishimaru, Takehisa
Shibata, Norio
Reddy, Dhande Sudhakar
Horikawa, Takao
Nakamura, Shuichi
Toru, Takeshi
DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
title DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
title_full DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
title_fullStr DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
title_full_unstemmed DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
title_short DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
title_sort dbfox-ph/metal complexes: evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
topic Preliminary Communication
url 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
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