A series of easily obtained pyrrolidine-based beta-amino alcohols derived from tartaric acid and primary amines was synthesized and used as chiral ligands in the enantioselective alkylation of benzaldehyde. Using diethylzinc, 1-phenyl-1-propanol was obtained with enantiomeric excesses of up to 80% when (3S,4S)-N-(1-naphthylmethyl)-3,4-dihydroxypyrrolidine was used. The nature of the N-substituent on the ligand, as well as the reaction temperature proved to significantly influence reaction product distribution as well as the enantiomeric excess of the chiral alcohol. (C) 2002 Elsevier Science B.V. All rights reserved.