Ros Ñíguez, Diego, Guillena, Gabriela, Alonso, Diego A.
Chiral 2-Aminobenzimidazoles in Deep Eutectic Mixtures: Recyclable Organocatalysts for the Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to β-Nitroalkenes
ACS Sustainable Chemistry & Engineering. 2017, 5(11): 10649-10656. doi:10.1021/acssuschemeng.7b02613
URI: http://hdl.handle.net/10045/71254
DOI: 10.1021/acssuschemeng.7b02613
ISSN: 2168-0485
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.
Keywords:Asymmetric organocatalysis, Benzimidazole, Deep eutectic solvents, Green chemistry, Conjugate addition
American Chemical Society
info:eu-repo/semantics/article