STUDY ON ASYMMETRIC REFORMATSKY REACTION

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.