Chiral discrimination promoted by (1S,2S)-1-phenyl-2-amino-1,3-propanediol derivatives in the asymmetric reformatsky reaction

Some 3-t-butyldimethylsilyloxy derivatives, synthesized from the cheap commercially available (1S,2S)-2-amino-1-phenyl-1,3-propanediol [(1S,2S)-1], have been successfully employed as new chiral ligands in the asymmetric Reformatsky reaction on aldehydic substrates. The influence both of the substrate and of the ligand on the stereochemical pathway has been investigated by varying the structure of the carbonyl substrate and of the optically active aminodiols. (C) 1995 Wiley-Liss, Inc.