Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent
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Título: | Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent |
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Autor/es: | Torregrosa-Chinillach, Alejandro | Carral-Menoyo, Asier | Gómez Bengoa, Enrique | Chinchilla, Rafael |
Grupo/s de investigación o GITE: | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Organocatalysis | Enantioselective α-nitrogenation | α,α-disubstituted aldehydes |
Fecha de publicación: | 25-oct-2022 |
Editor: | American Chemical Society |
Cita bibliográfica: | The Journal of Organic Chemistry. 2022, 87(21): 14507-14513. https://doi.org/10.1021/acs.joc.2c01919 |
Resumen: | A highly efficient enantioselective α-nitrogenation method of α,α-disubstituted aldehydes with azodicarboxylates promoted by a chiral carbamate-monoprotected cyclohexa-1,2-diamine as organocatalyst has been developed. The process was carried out without any solvent, and the corresponding α,α-disubstituted α-nitrogenated aldehydes were obtained with excellent yields and enantioselectivities up to 99% ee. The sustainability of the procedure was established through the calculation of green metrics, such as EcoScale and E-factor. In addition, theoretical calculations have been used to justify the obtained enantioselectivity sense. |
Patrocinador/es: | This work was funded by the Spanish Ministry of Economy, Industry and Competitiveness (PGC2018-096616-B-I00), the Spanish Ministry of Science and Innovation (PID2019-110008GB-I00), and the University of Alicante (VIGROB-173). We also thank SGIker (UPV/EHU) for providing human and computational resources. |
URI: | http://hdl.handle.net/10045/128876 |
ISSN: | 0022-3263 (Print) | 1520-6904 (Online) |
DOI: | 10.1021/acs.joc.2c01919 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2022 The Authors. Published by American Chemical Society. Creative Commons Attribution 4.0 International License (CC BY 4.0) |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1021/acs.joc.2c01919 |
Aparece en las colecciones: | INV - CESO - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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Torregrosa-Chinillach_etal_2022_JOrgChem.pdf | 2,34 MB | Adobe PDF | Abrir Vista previa | |
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