Asymmetric hydroamination of acrylonitrile derivatives catalyzed by Ni(II)-complexes

Chiral ferrocenyl tridentate phosphine ligands were synthesized and used in asymmetric hydroamination reactions catalyzed by Ni(II)-complexes. Compounds of the type [Ni(PPP)L](2+), where L is a chloride, solvent molecule or a coordinated substrate, were isolated. The efficiency of these complexes in asymmetric catalysis was high when aliphatic or aromatic amines were reacted with electron-poor olefins, especially with acrylonitrile derivatives. This hydroamination reaction affords up to 95% enantioselectivity at -80 degrees C for the addition of morpholine to methacrylonitrile (69% ee at room temperature). (C) 2008 Elsevier Ltd. All rights reserved.