Abstract
Chiral ligand-modified metal nanoparticles possess an attractive potential for application in asymmetric synthesis. This article focuses on chiral-nanoparticle-catalyzed asymmetric C-C bond formation reactions and discusses the nature of the active species.
Highlights
In a report from the same group in 2008, the enantioselectivity of this system was improved (82% ee) by changing the chiral modifier to a ferrocenyl phosphine ligand 10.122 As in the case of the Pd/Al2O3–BINAP system, no dependence of enantioselectivity on temperature was observed (60 and 120 1C), while the enantioselectivity was decreased by increasing the reaction temperature from 85% ee at 60 1C to 55% ee at 120 1C in the Scheme 5 Asymmetric allylic alkylation of rac-8 with dimethyl malonate by Pd catalyst
The recent reports that we reviewed clearly showed the potential of chiral NP catalysts for asymmetric hydrogenation, and for various types of asymmetric C–C bond formation reactions
Chiral NPs can be generated from metal precursors and chiral modifiers
Summary
Rapid progress has been made in the field of homogeneous chiral metal complexes and many types of difficult transformations have been realized, including asymmetric C–C bond formation, to construct complicated molecular structures with high selectivity.[1,2] the application of these homogeneous catalysts to large-scale industrial processes is still limited.[3,4,5,6,7,8,9] This is because industry generally prefers heterogeneous catalysts because of their great advantages, such as low cost, reusability, avoidance of metal contamination of products, and the availability for reaction integration such as in continuous flow systems and tandem reactions.[10,11,12,13,14] One of the common strategies to convert homogeneous catalysts to heterogeneous catalysts is immobilization. Shu Kobayashi studied at the University of Tokyo, receiving his PhD in 1988 working under the direction of Professor T. In 2007, he was appointed to his current position as professor of organic chemistry in the Department of Chemistry, Faculty of Science, The University of Tokyo. Asymmetric C–C bond formation reactions catalyzed by chiral NPs are a challenging topic and less well developed, judging from the mechanism of the corresponding homogeneous metal complex system. The mechanism of chiral induction is more complicated and multicoordination of both chiral modifier and substrates to NPs is required in transition states This type of multicoordination may cause the metal to leach from supports or the decomposition of NPs to form molecular complexes.
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