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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2016
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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. |
format | Online Article Text |
id | pubmed-4902052 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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