Abstract
A chiral primary amine-salicylamide is used as an organocatalyst for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides and nitroalkenes. The reactions are performed in deep eutectic solvents as reaction media at room temperature, leading to the corresponding adducts with enantioselectivities up to 88% (for maleimides) and 80% (for nitroalkenes). Catalyst and solvent can be recovered and reused.
Highlights
Traditional volatile organic compounds (VOCs) are the common solvents for performing organic reactions from an environmental point of view, they show many intrinsic drawbacks, such as accumulation in the atmosphere due to their low boiling points, flammability, toxicity and non-biodegradability
Probably the most attractive methodology for the enantioselective preparation of functionalized molecules in organic synthesis is the use of asymmetric organocatalysis, since metal-free small organic compounds are used as catalysts under usually very mild and simple reaction conditions [12,13]
The primary amine-salicylamide 8 was prepared as described by monoamidation of (1R,2R)The primary amine-salicylamide 8 was prepared as described by monoamidation of cyclohexane-1,2-diamine with phenyl salicylate in refluxing propan-2-ol [25]
Summary
Traditional volatile organic compounds (VOCs) are the common solvents for performing organic reactions from an environmental point of view, they show many intrinsic drawbacks, such as accumulation in the atmosphere due to their low boiling points, flammability, toxicity and non-biodegradability For all these reasons several greener and friendlier synthetic methodologies based on alternative reaction media have been developed, all of them having certain number of advantages, as well as disadvantages [1,2]. Probably the most attractive methodology for the enantioselective preparation of functionalized molecules in organic synthesis is the use of asymmetric organocatalysis, since metal-free small organic compounds are used as catalysts under usually very mild and simple reaction conditions [12,13] This methodology maintains sustainability in organic synthesis and provides many advantages, such as accessibility, inexpensive catalysts and reduced toxicity. Most of these asymmetric processes are carried out using environmentally unfriendly VOCs as reaction media, efforts have been devoted to achieving more sustainable synthetic procedures [14]
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