Sustainable Organocatalyzed Enantioselective Catalytic Michael Additions in Betaine-Derived Deep Eutectic Solvents

The organocatalyst cinchonidine-squaramide was immobilized within three different deep eutectic solvents (DESs): betaine:D-sor-bitol:water, betaine: D-xylitol:water, and betaine:D-mannitol:water and evaluated in a well-known asymmetric Michael addition. These reactions provided excellent yields (up to 99%) and enantioselectivities (up to 98%) using only 1 mol% of organocatalyst. It was also possible to achieve 9 cycles in reactions with DES (betaine:D-sorbitol:water), proving the high recyclability of this system. In the reactions realized with only 0.5 mol% of organocatalyst, it was possible to achieve 5 cycles, and the products were obtained with high yields (up to 95%) and excellent enantioselectivities (up to 94%), using DES (betaine:D-sorbitol:water).

Automated summary

The organocatalyst cinchonidine-squaramide was immobilized within three different deep eutectic solvents (DESs) and evaluated in an asymmetric Michael addition reaction. The results showed excellent yields (up to 99%) and enantioselectivities (up to 98%) using only 1 mol% of organocatalyst. The high recyclability of this system was demonstrated with 9 cycles using DES (betaine:D-sorbitol:water), and 5 cycles were achieved with only 0.5 mol% of organocatalyst, obtaining products with high yields (up to 95%) and excellent enantioselectivities (up to 94%).