European Journal of Organic Chemistry p. 4205 - 4211 (2011)
Update date:2022-08-02
Topics: Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation Substituent effect Catalyst efficiency
Zhang, Bo
Wang, Hui
Lin, Guo-Qiang
Xu, Ming-Hua
The use of unsymmetrical vicinal diamines as ligands for Ru-catalyzed asymmetric transfer hydrogenation is described. With a SmI2-mediated cross-coupling protocol, a series of enantiomerically pure unsymmetrical vicinal diamines were readily prepared and examined in the asymmetric transfer hydrogenation. It was found that an aromatic substituent on the carbon bearing the-NHTs group and a bulky alkyl substituent on the other side, are both very important for the effectiveness of the ligand, suggesting that the substituent has a dramatic effect on the catalyst efficiency. With ligand 8, excellent enantioselectivities that are comparable to N-tosyl-1,2-diphenylethane-1,2- diamine (TsDPEN) were achieved. The results provide some helpful information on the mechanism of Ru-catalyzed asymmetric transfer hydrogenation. A series of unsymmetrical vicinal diamines were prepared and examined as chiral ligands for Ru-catalyzed asymmetric transfer hydrogenation.
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