Co-metal-free enantioselective conjugate addition reactions of zinc reagents

Asymmetric conjugate addition of diethylzinc to cinnamaldehyde in a co-metal-free fashion by using N,O-ligands with planar and central chirality is described. Different modulations of the ligand structure, including several combinations of the chiral units, indicate that a 2.2]paracyclophane backbone is essential for the activity and the enantioselectivity of the generated active catalyst. By using the optimized ligand, an isolated yield of 90 % was obtained with up to 99 % ee.