Enantioselective alkylation of carbonyl compounds is a challenged domain of asymmetric C-C bond formation. Particularly, asymmetric addition of diethylzinc to aldehydes is one of the important synthetic methods for the preparation of optically active secondary alcohols, and numerious efforts have been made to find effective chiral ligands. To date, most of the successful results were obtained by using sterically constrained β-amino alcohols such as N,Ndialkylated norephedrine derivatives. Extensive studies by Soai on the effect of ligand structure on enantioselectivity indicated that the chain length of the N-alkyl substituent is very imporant. Thus, the catalyst with N-alkyl substituents of a chain length of four carbons, 1 (DBNE), gave the best results in dialkylzinc addition to various aliphatic (87-93% ee) and aromatic (90-95% ee) aldehydes. It has been recently reported that some azacyclo β-amino alcohols (2 and 3) are among the most efficient chiral ligand in catalytic asymmetric reaction. Employment of conformationally rigid rings such as pyrrolidine and piperidine would provide beneficial on controlling precisely the stereochemical sense in asymmetric catalysis. Here we wish to report a new-type of amino alcohol (4) bearing isoindolinyl moiety as a face blocker and its catalytic efficiency in asymmetric addition of diethylzinc to various aldehydes. The isoindolinyl moiety may possess similar steric and electronic properties with substituted groups at nitrogen of the DBNE, but conformationally more rigid. Hence, compare to DBNE or pyrrolidine ligand 2, it may block effectively the approach of the attacking species to one of the enantiotopic faces of aldehydes. The (1S,2R)-1-phenyl-2-(2-isoindolinyl)-1-propanol[(1S,2R)4] was easily prepared in 95% yield by the reaction of (1S,2R)-norephedrine with α,α'-dibromoxylene in ethanol in the presence of potassium carbonate (Scheme 1). In order to examine the catalytic ability of the ligand 4, the enantioselective addition of diethylzinc to aldehydes was Figure 1. β-Aminoalcohols for diethylzinc addition.