A catalytic system based on deep eutectic solvents 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 VOC as 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 the recyclability of the catalytic system is possible at least for 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. NMR studies have Page 1 of 23 ACS Paragon Plus Environment ACS Sustainable Chemistry & Engineering 2 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.
The enantioselective α-amination of 1,3-dicarbonyl compounds has been performed using deep eutectic solvents (DES) as a reaction media and chiral 2-amino benzimidazole-derived compounds as a catalytic system. With this procedure, the use of toxic volatile organic compounds (VOCs) as reaction media is avoided. Furthermore, highly functionalized chiral molecules, which are important intermediates for the natural product synthesis, are synthetized by an efficient and stereoselective protocol. Moreover, the reaction can be done on a preparative scale, with the recycling of the catalytic system being possible for at least five consecutive reaction runs. This procedure represents a cheap, simple, clean, and scalable method that meets most of the principles to be considered a green and sustainable process.
<div><div><div><p>In this paper L-Proline-based Chiral Deep Eutectic Solvents (CDESs) were prepared and used as green and organocatalytic reaction media in a probe asymmetric Michael addition; in this reaction the L-Proline acts as solvent component as well as chiral organocatalyst. The results were analysed with NMR studies taking in account the availability of the L-Proline considering the strength of the association of it with the counterpart of the liquids. With DFT studies, the geometry and energy of the adducts are showed and a qualitative rationale to the reaction stereoisomers distribution is given.</p></div></div></div>
The enantioselective alpha-amination of 1,3-dicarbonyl compounds has been performed using a catalytic system based on deep eutectic solvents (DES) and chiral 2-amino benzimidazole-derived organocatalysts. This procedure avoids the use of toxic volatile organic compounds (VOCs) as a reaction medium, providing access to highly functionalized chiral molecules, which are important intermediates for the natural product synthesis, 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 five times, leading to a clean, cheap, simple, and scalable procedure that meets most of the criteria required to be a green and sustainable process.
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