Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 11, Issue 14, Pages 2072-2077Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201600640
Keywords
asymmetric catalysis; heterogeneous catalyst; immobilization; silica; supported catalysts
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Funding
- China National Natural Science Foundation [21402120]
- Shanghai Sciences and Technologies Development Fund [13ZR1458700]
- CSIRT [IRT1269]
- Shanghai Municipal Education Commission [14YZ074]
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A cinchona alkaloid-functionalized heterogeneous catalyst is prepared through a thiol-ene click reaction of chiral N-(3,5-ditrifluoromethylbenzyl)quininium bromide and a mesostructured silica, which is obtained by co-condensation of 1,2-bis(triethoxysilyl)ethane and 3-(triethoxysilyl)propane-1-thiol. Structural analyses and characterizations disclose its well-defined chiral single-site active center, and electron microscopy images reveal its monodisperse property. As a heterogenous catalyst, it enables an efficient asymmetric epoxidation of achiral -trifluoromethyl-,-disubstituted enones, the obtained chiral products can then be converted easily into enriched chiral -trifluoromethyl--hydroxy ketones through a sequential epoxidation-relay reduction process. Furthermore, such a heterogeneous catalyst can be recovered conveniently and reused in asymmetric epoxidation of 4,4,4-trifluoro-1,3-diphenylbut-2-enone, showing an attractive feature in a practical construction of enriched chiral -CF3-substituted molecules.
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