Four new chiral aminodiols 1-4, which were prepared from methyl L proline in 2 steps, were applied in the enantioselective addition of diethylzinc to benzaldehyde. The results indicated that the enantioselectivities enhance with increasing the bulkiness of substituents on chiral ligands and with chiral ligand 4 giving the best result. When ligand 4 was used to catalyze the enantioselective addition of diethylzinc to aromatic aldehydes, the substituents affect the enantioselectivities slightly and 1 naphthaldehyde gives the best enantiomeric excess(up to 75.3% ). On the other hand, 4 (dimethylamino)benzaldehyde gives a low enantiomeric excess, which may most likely arise from a non steroselective ethyl transfer to aldehyde promoted by zinc coordination of amino group. For aliphatic aldehydes, poor enantiomeric excesses are generally given.
