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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...

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Autores principales: García-Mingüens, Eduardo, Ferrándiz-Saperas, Marcos, de Gracia Retamosa, M., Nájera, Carmen, Yus, Miguel, Sansano, José M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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.
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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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