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

Fonseca, Daniela P.; Amorim, Ana C.; Carreiro, Elisabete P.; Ramalho, João P. Prates; Hermann, Gesine J.; Federsel, Hans Jürgen; Duarte, Ana Rita C.; Burke, Anthony J.

http://hdl.handle.net/10362/158161

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Autores

Fonseca, Daniela P.

Amorim, Ana C.

Carreiro, Elisabete P.

Ramalho, João P. Prates

Hermann, Gesine J.

Federsel, Hans Jürgen

Duarte, Ana Rita C.

Burke, Anthony J.

Resumo(s)

The organocatalyst cinchonidine-squaramide was immobilized within three different deep eutectic solvents (DESs): betaine:D-sorbitol: 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 (upto 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).

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Palavras-chave

betaine cinchonidine-squaramide deep eutectic solvent (DES) immobilization organocatalysis Catalysis Biomaterials Materials Science (miscellaneous) Organic Chemistry