Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines
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Título: | Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines |
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Autor/es: | García-Mingüens, Eduardo | Ferrándiz-Saperas, Marcos | Retamosa, Maria de Gracia | Nájera, Carmen | Yus, Miguel | Sansano, Jose M. |
Grupo/s de investigación o GITE: | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Nitroprolinates | Enantioseletive cycloaddition | Phosphoramidite | Azomethine ylides | Diamines |
Fecha de publicación: | 18-jul-2022 |
Editor: | MDPI |
Cita bibliográfica: | García-Mingüens E, Ferrándiz-Saperas M, de Gracia Retamosa M, Nájera C, Yus M, Sansano JM. Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines. Molecules. 2022; 27(14):4579. https://doi.org/10.3390/molecules27144579 |
Resumen: | 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. |
Patrocinador/es: | We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (project RED2018-102387-T) the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P, CTQ2016-80375-P, CTQ2017-82935-P and PID2019-107268GB-I00), the Generalitat Valenciana (IDIFEDER/2021/013, CIDEGENT/2020/058 and APOTIP/2020/002), Medalchemy S. L. (Medalchemy-18T) and the University of Alicante (VIGROB-068, UAUSTI21-05). |
URI: | http://hdl.handle.net/10045/126189 |
ISSN: | 1420-3049 |
DOI: | 10.3390/molecules27144579 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2022 by the authors. 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/). |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.3390/molecules27144579 |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
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