Chiral 2-Aminobenzimidazoles in Deep Eutectic Mixtures: Recyclable Organocatalysts for the Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to β-Nitroalkenes
| Autor: | Gabriela Guillena, Diego Ros Ñíguez, Diego A. Alonso |
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| Přispěvatelé: | Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Catálisis Estereoselectiva en Síntesis Orgánica (CESO) |
| Rok vydání: | 2017 |
| Předmět: |
Green chemistry
Benzimidazole 010405 organic chemistry Renewable Energy Sustainability and the Environment Chemistry General Chemical Engineering Conjugate addition Deep eutectic solvents Enantioselective synthesis General Chemistry 010402 general chemistry Sustainable process 01 natural sciences 0104 chemical sciences Catalysis Asymmetric organocatalysis chemistry.chemical_compound Química Orgánica Michael reaction Environmental Chemistry Organic chemistry Eutectic system |
| Zdroj: | RUA. Repositorio Institucional de la Universidad de Alicante Universidad de Alicante (UA) |
| Popis: | A catalytic system based on deep eutectic solvents (DESs) and chiral 2-amino benzimidazole organocatalysts is used to promote the enantioselective addition of 1,3-dicarbonyl compounds to β-nitrostyrenes. This procedure avoids the use of toxic volitile organic compounds (VOCs) as a reaction medium, providing access to highly functionalized chiral molecules in a selective and efficient manner. Furthermore, the reaction can be performed on a large scale and recycling the catalytic system is possible for at least four times, leading to a clean, cheap, simple, and scalable procedure that meets most of the criteria required to be a green and sustainable process. Nuclear magnetic resonance studies have confirmed the key role of the hydrogen-bonding interactions between the DES and the chiral organocatalyst, which allow their recovery and the recyclability of the system. Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P). University of Alicante (UAUSTI16-03, AUSTI16-10, VIGROB-173, VIGROB-285). |
| Databáze: | OpenAIRE |
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