Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C1-Symmetric Aminopinane-Derived Ligand.

A novel C1-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(-)-isopinocampheylamine and 1-methyl-2- imidazolecarboxaldehyde. In combination with Cu(OAc)₂.H₂O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes with high yields (up to 97%) and moderate enantioselectivities (up to 67% ee). The reactions with benzaldehyde required prolonged reaction time that resulted in diminished yields, but accompanied with ee-values in the 55%-76% range. [ABSTRACT FROM AUTHOR]