Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 32, Pages 9969-9978Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402709
Keywords
asymmetric catalysis; dendrimers; hydrogenation; ligands; ruthenium
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Funding
- National Natural Science Foundation of China [21232008, 21290194, 21221002]
- National Basic Research Program of China (973 program) [2010CB833300]
- ICCAS (Institute of Chemistry), Chinese Academy of Sciences
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A series of tunable G(0)-G(3) dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of beta-ketoesters, alpha-aketoesters, and alpha-ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.
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