Cu (II)-catalyzed asymmetric Henry reaction with a novel C1-symmetric aminopinane-derived ligand

Abstract

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.