Chiral 2-Aminobenzimidazoles in Deep Eutectic Mixtures: Recyclable Organocatalysts for the Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to β-Nitroalkenes
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Title: | Chiral 2-Aminobenzimidazoles in Deep Eutectic Mixtures: Recyclable Organocatalysts for the Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to β-Nitroalkenes |
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Authors: | Ros Ñíguez, Diego | Guillena, Gabriela | Alonso, Diego A. |
Research Group/s: | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Asymmetric organocatalysis | Benzimidazole | Deep eutectic solvents | Green chemistry | Conjugate addition |
Knowledge Area: | Química Orgánica |
Issue Date: | 6-Oct-2017 |
Publisher: | American Chemical Society |
Citation: | ACS Sustainable Chemistry & Engineering. 2017, 5(11): 10649-10656. doi:10.1021/acssuschemeng.7b02613 |
Abstract: | 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. |
Sponsor: | Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P). University of Alicante (UAUSTI16-03, AUSTI16-10, VIGROB-173, VIGROB-285). |
URI: | http://hdl.handle.net/10045/71254 |
ISSN: | 2168-0485 |
DOI: | 10.1021/acssuschemeng.7b02613 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2017 American Chemical Society |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1021/acssuschemeng.7b02613 |
Appears in Collections: | INV - CESO - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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2017_Ros_etal_ACSSustainableChemEng_final.pdf | Versión final (acceso restringido) | 1,53 MB | Adobe PDF | Open Request a copy |
2017_Ros_etal_ACSSustainableChemEng_accepted.pdf | Accepted Manuscript (acceso abierto) | 487,32 kB | Adobe PDF | Open Preview |
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