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Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines †
The enantioselective 1,3-dipolar cycloaddition between imino esters and (Z)-nitroalkenes bearing a masked amino group in the β-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly applied to the study of the scope of the reaction. The de...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9316397/ https://www.ncbi.nlm.nih.gov/pubmed/35889453 http://dx.doi.org/10.3390/molecules27144579 |
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author | García-Mingüens, Eduardo Ferrándiz-Saperas, Marcos de Gracia Retamosa, M. Nájera, Carmen Yus, Miguel Sansano, José M. |
author_facet | García-Mingüens, Eduardo Ferrándiz-Saperas, Marcos de Gracia Retamosa, M. Nájera, Carmen Yus, Miguel Sansano, José M. |
author_sort | García-Mingüens, Eduardo |
collection | PubMed |
description | The enantioselective 1,3-dipolar cycloaddition between imino esters and (Z)-nitroalkenes bearing a masked amino group in the β-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly applied to the study of the scope of the reaction. The determination of the absolute configuration was evaluated using NMR experiments and electronic circular dichroism (ECD). The reduction and hydrolysis of both groups was performed to generate in an excellent enantiomeric ratio the corresponding cis-2,3-diaminoprolinate. |
format | Online Article Text |
id | pubmed-9316397 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-93163972022-07-27 Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines † García-Mingüens, Eduardo Ferrándiz-Saperas, Marcos de Gracia Retamosa, M. Nájera, Carmen Yus, Miguel Sansano, José M. Molecules Article The enantioselective 1,3-dipolar cycloaddition between imino esters and (Z)-nitroalkenes bearing a masked amino group in the β-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly applied to the study of the scope of the reaction. The determination of the absolute configuration was evaluated using NMR experiments and electronic circular dichroism (ECD). The reduction and hydrolysis of both groups was performed to generate in an excellent enantiomeric ratio the corresponding cis-2,3-diaminoprolinate. MDPI 2022-07-18 /pmc/articles/PMC9316397/ /pubmed/35889453 http://dx.doi.org/10.3390/molecules27144579 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article García-Mingüens, Eduardo Ferrándiz-Saperas, Marcos de Gracia Retamosa, M. Nájera, Carmen Yus, Miguel Sansano, José M. Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines † |
title | Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines † |
title_full | Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines † |
title_fullStr | Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines † |
title_full_unstemmed | Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines † |
title_short | Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines † |
title_sort | enantioselective 1,3-dipolar cycloaddition using (z)-α-amidonitroalkenes as a key step to the access to chiral cis-3,4-diaminopyrrolidines † |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9316397/ https://www.ncbi.nlm.nih.gov/pubmed/35889453 http://dx.doi.org/10.3390/molecules27144579 |
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