Enantioselective Hydrosilylation of Imines Catalyzed by Diamine-Zinc Complexes

• Published in: Bulletin of the Korean Chemical Society Vol. 32; no. 8; pp. 2960 - 2964
• Main Authors: Park, Bu-Mahn, Feng, Xinhui, Yun, Jaesook
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 20.08.2011; 대한화학회
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; 화학; ASYMMETRIC HYDROSILYLATION; KETONES; Amines; Imines; REDUCTION; CARBONYL-COMPOUNDS; Hydrosilylation; Enantioselectiviy; Zinc; POLYMETHYLHYDROSILOXANE
• ISSN: 0253-2964; 1229-5949
• DOI: 10.5012/bkcs.2011.32.8.2960

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-dipheny1-1,2-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.