期刊
SUSTAINABLE CHEMISTRY AND PHARMACY
卷 13, 期 -, 页码 -出版社
ELSEVIER
DOI: 10.1016/j.scp.2019.100152
关键词
Magnetic nano particles; Recyclable catalysts; Macrocyclic effect; Direct aldol reaction
资金
- Taiwan Ministry of Science and Technology [MOST 103-2113-M-259-010, NSC 100-2622-M-259-001-CC2]
Chiral amine and their derivatives have been proved to be powerful organocatalysts for asymmetric transformations. There is a trend to combine organocatalyst with sustainable matrix, such as, magnetic nanoparticles (MNPs) to form a selective and recyclable catalyst. Therefore, silica-coated Fe3O4 MNP was fabricated to establish a large macrocycle with glutamate (MNP-17 and 18), Pro-Glu (MNP-21), or cyclohexyl-1,2-diamine (MNP-28, 29, and 30). Their bifunctional enamine activities were evaluated with direct aldol reaction. Among them, MNP-30 having the largest macrocyclic ring and the longest lipophilic chain achieved better yield and ee value (up to 96%). It seems the affinity toward substrate was enhanced by the macrocyclic effect. The rigidity of cyclohexyl-1,2-diamine contributed the enantioselectivity. Moreover, MNP-30 is recyclable and stayed on high activity and enantioselectivity after 3 recycles.
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