Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Received : 2011.03.09
  • Accepted : 2011.03.24
  • Published : 2011.08.20
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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.

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