Abstract
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.
Highlights
Asymmetric organocatalysis is an extremely attractive methodology for the preparation of functionalized chiral molecules and natural products, since small organic compounds are used as catalysts under very mild and simple reaction conditions [1,2,3]
We have demonstrated that the catalytic system based on the deep eutectic solvent choline and chiral chiral 2-aminobenzimidazole
Reactions under argon atmosphere were carried out in oven-dried glassware sealed with purification
Summary
Asymmetric organocatalysis is an extremely attractive methodology for the preparation of functionalized chiral molecules and natural products, since small organic compounds are used as catalysts under very mild and simple reaction conditions [1,2,3]. Asymmetric organocatalysis has become such an effective method of maintaining sustainability in organic synthesis as it provides many advantages, such as accessibility, low molecular weight, inexpensive catalysts and reduced toxicity. A deep eutectic solvent is a mixture between two or more components, one acting as hydrogen bond acceptor and the other as donor, having a melting point lower than the melting point of each one of the components. This behavior is due to hydrogen bond interactions between the acceptor and donor species. The association of these reaction media with asymmetric organocatalyzed processes [13,14] has been envisaged as a new and bright approach to advance sustainable processes
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