Enantioselective Catalytic Aldol Reactions in the Presence of Knoevenagel Nucleophiles: A Chemoselective Switch Optimized in Deep Eutectic Solvents Using Mechanochemistry
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Título: | Enantioselective Catalytic Aldol Reactions in the Presence of Knoevenagel Nucleophiles: A Chemoselective Switch Optimized in Deep Eutectic Solvents Using Mechanochemistry |
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Autor/es: | Al Beiruty, Hanaa | Zhylinska, Sofiia-Stefaniia | Kutateladze, Nino | Cheong, Hayley Kay Tinn | Ñíguez, José A. | Burlingham, Sarah-Jayne | Marset, Xavier | Guillena, Gabriela | Chinchilla, Rafael | Alonso, Diego A. | Nugent, Thomas C. |
Grupo/s de investigación o GITE: | Alternative Methodologies In Chemistry (AMIC) | 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: | Organic synthesis | Green chemistry | Organocatalysis | In-water conditions | Deep eutectic solvents | Aldol reaction | Knoevenagel reaction |
Fecha de publicación: | 19-dic-2023 |
Editor: | MDPI |
Cita bibliográfica: | Al Beiruty H, Zhylinska S-S, Kutateladze N, Cheong HKT, Ñíguez JA, Burlingham SJ, Marset X, Guillena G, Chinchilla R, Alonso DA, et al. Enantioselective Catalytic Aldol Reactions in the Presence of Knoevenagel Nucleophiles: A Chemoselective Switch Optimized in Deep Eutectic Solvents Using Mechanochemistry. Molecules. 2024; 29(1):4. https://doi.org/10.3390/molecules29010004 |
Resumen: | In the presence of different nucleophilic Knoevenagel competitors, cyclic and acyclic ketones have been shown to undergo highly chemoselective aldol reactions with aldehydes. In doing so, the substrate breadth for this emerging methodology has been significantly broadened. The method is also no longer beholden to proline-based catalyst templates, e.g., commercially available O-t-Bu-L-threonine is advantageous for acyclic ketones. The key insight was to exploit water-based mediums under conventional (in-water) and non-conventional (deep eutectic solvents) conditions. With few exceptions, high aldol-to-Knoevenagel chemoselectivity (>10:1) and good product profiles (yield, dr, and ee) were observed, but only in DESs (deep eutectic solvents) in conjunction with ball milling did short reaction times occur. |
Patrocinador/es: | The authors acknowledge the financial support by the Spanish Ministerio de Ciencia e Innovación (PID2021-127332NB-I00), the Generalitat Valenciana (AICO 2021/013) and the University of Alicante (VIGROB-173 and UAUSTI 2022). This research was financially supported by Constructor University Bremen. |
URI: | http://hdl.handle.net/10045/139560 |
ISSN: | 1420-3049 |
DOI: | 10.3390/molecules29010004 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2023 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/molecules29010004 |
Aparece en las colecciones: | INV - AMIC - Artículos de Revistas INV - CESO - Artículos de Revistas |
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Al-Beiruty_etal_2024_Molecules.pdf | 8,62 MB | Adobe PDF | Abrir Vista previa | |
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