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Proline‐derived Monodentate Organocatalyst for Asymmetric Reduction of Imine with HSiCl 3
Author(s) -
Li Qiang,
Li Yuan,
Yang Qingbiao,
Bai Fuquan
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902699
Subject(s) - chemistry , catalysis , denticity , moiety , nucleophile , ligand (biochemistry) , combinatorial chemistry , stacking , imine , organic chemistry , metal , biochemistry , receptor
An organocatalyst was developed for the reduction of imines with a rational reaction process and new mechanism that the hydrogen proton triggered the reaction other than the nucleophilic hydrogen from HSiCl 3 based on extensive theoretical calculations, which was different from the previous study. The Electronic Static Potential and Fukui function indicate that the azobenzene moiety of the catalyst effectively is beneficial to enhance the attraction of electrons and stabilize the π‐π stacking between the catalyst and reactant. Furthermore, the entire catalytic process was simulated by theoretical calculations, which indicated that the single carbonyl ligand of the N –formyl–proline derivative activated HSiCl 3 , instead of the bidentate ligand. Utilizing the concept of green chemistry, the catalyst could be recycled using Fe 3 O 4 magnetic nanoparticles through the self‐assembly method with only a slight decrease in activity.