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Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions

The catalytic activity of different supported bifunctional thioureas on sulfonylpolystyrene resins has been studied in the nitro-Michael addition of different nucleophiles to trans-β-nitrostyrene derivatives. The activity of the catalysts depends on the length of the tether linking the chiral thiour...

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Autores principales: Andrés, José M, Ceballos, Miriam, Maestro, Alicia, Sanz, Isabel, Pedrosa, Rafael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4902052/
https://www.ncbi.nlm.nih.gov/pubmed/27340453
http://dx.doi.org/10.3762/bjoc.12.61
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author Andrés, José M
Ceballos, Miriam
Maestro, Alicia
Sanz, Isabel
Pedrosa, Rafael
author_facet Andrés, José M
Ceballos, Miriam
Maestro, Alicia
Sanz, Isabel
Pedrosa, Rafael
author_sort Andrés, José M
collection PubMed
description The catalytic activity of different supported bifunctional thioureas on sulfonylpolystyrene resins has been studied in the nitro-Michael addition of different nucleophiles to trans-β-nitrostyrene derivatives. The activity of the catalysts depends on the length of the tether linking the chiral thiourea to the polymer. The best results were obtained with the thiourea derived from (L)-valine and 1,6-hexanediamine. The catalysts can be used in only 2 mol % loading, and reused for at least four cycles in neat conditions. The ball milling promoted additions also worked very well.
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spelling pubmed-49020522016-06-23 Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions Andrés, José M Ceballos, Miriam Maestro, Alicia Sanz, Isabel Pedrosa, Rafael Beilstein J Org Chem Full Research Paper The catalytic activity of different supported bifunctional thioureas on sulfonylpolystyrene resins has been studied in the nitro-Michael addition of different nucleophiles to trans-β-nitrostyrene derivatives. The activity of the catalysts depends on the length of the tether linking the chiral thiourea to the polymer. The best results were obtained with the thiourea derived from (L)-valine and 1,6-hexanediamine. The catalysts can be used in only 2 mol % loading, and reused for at least four cycles in neat conditions. The ball milling promoted additions also worked very well. Beilstein-Institut 2016-04-01 /pmc/articles/PMC4902052/ /pubmed/27340453 http://dx.doi.org/10.3762/bjoc.12.61 Text en Copyright © 2016, Andrés 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 Full Research Paper
Andrés, José M
Ceballos, Miriam
Maestro, Alicia
Sanz, Isabel
Pedrosa, Rafael
Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
title Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
title_full Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
title_fullStr Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
title_full_unstemmed Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
title_short Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
title_sort supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-michael reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4902052/
https://www.ncbi.nlm.nih.gov/pubmed/27340453
http://dx.doi.org/10.3762/bjoc.12.61
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