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http://dx.doi.org/10.5012/bkcs.2011.32.8.2960

Enantioselective Hydrosilylation of Imines Catalyzed by Diamine-Zinc Complexes  

Park, Bu-Mahn (Department of Chemistry and Institute of Basic Science, Sungkyunkwan University)
Feng, Xinhui (Department of Chemistry and Institute of Basic Science, Sungkyunkwan University)
Yun, Jae-Sook (Department of Chemistry and Institute of Basic Science, Sungkyunkwan University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.spc8, 2011 , pp. 2960-2964 More about this Journal
Abstract
The efficient asymmetric hydrosilylation of imines in the presence of polymethylhydrosiloxane has been investigated by screening chiral diamine-zinc complexes. A series of chiral diamine ligands were prepared from optically pure 1,2-diphenyl-1,2-ethanediamine and screened for effectiveness. N-Benzylic substituents were required for high enantioselectivity; ligands with bulky groups or extra coordinating groups such as OH and S lowered the catalytic activity. The level of asymmetric induction was usually in >90% ee range for aromatic imine substrates. A linear correlation between the ee of the ligand and that of the product was observed, indicating the presence of a 1:1 ratio of ligand to metal coordination in the active catalytic complex.
Keywords
Amines; Enantioselectiviy; Hydrosilylation; Imines; Zinc;
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