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

被引:3
|
作者
Fonseca, Daniela P. [1 ]
Amorim, Ana C. [2 ,3 ]
Carreiro, Elisabete P. [4 ]
Ramalho, Joao P. Prates [1 ,3 ,4 ]
Hermann, Gesine J. [2 ]
Federsel, Hans-Juergen [5 ]
Duarte, Ana Rita C. [6 ]
Burke, Anthony J. [1 ,4 ,7 ]
机构
[1] Univ Evora, Sch Sci & Technol, Chem & Biochem Dept, Evora, Portugal
[2] Chiratecnics, LDA, PO, Rossio, P-7006802 Evora, Portugal
[3] Univ Evora, Lab 007, Bldg A Colegio Pedro Fonseca,PITE Ind & Technol Pk, P-7000 Evora, Portugal
[4] Univ Evora, Inst Res & Adv Studies, LAQV REQUIMTE, Rua Romao Ramalho 59, P-7000671 Evora, Portugal
[5] Res Inst Sweden, RISE, Box 5607, S-11486 Stockholm, Sweden
[6] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, LAQV REQUIMTE, P-2829516 Caparica, Portugal
[7] Univ Coimbra, Fac Pharm, Polodas Ciencias Saude, Azinhaga Santa Comba, P-3000548 Coimbra, Portugal
来源
SYNOPEN | 2023年 / 07卷 / 03期
关键词
cinchonidine-squaramide; betaine; deep eutectic solvent (DES); immobilization; organocatalysis;
D O I
10.1055/a-2117-9971
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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).
引用
收藏
页码:374 / 380
页数:7
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