A series of derivatives of (1R,2S) or (1S,2R)-2-amino-1,2-diphenyl eth
anol (1) have been applied to asymmetric Reformatsky reaction of benza
ldehyde (2) with alkyl bromoacetate (3). The influence of structure of
the chiral aminoalcohol on the enantioselectivity was studied. Then s
everal reaction parameters were also researched, including the amount
of chiral ligand, solvent effect and alternation of the substrate. Fur
thermore, 0.25 mol% of the chiral ligands were employed in the reactio
n of benzaldehyde with optically active menthyl bromoacetate and moder
ate enantioselectivity has been achieved via matched double chiral ind
uction. The effect of various experimental methods on the enantioselec
tivity was also studied. Finally, a catalytic asymmetric mechanism was
suggested. Moreover, the most experimental facts can be explained by
the mechanism proposed.