Enantioselective synthesis of fluorinated alpha-amino acids and derivatives in combination with ring-closing metathesis: Intramolecular pi-stacking interactions as a source of stereocontrol

[GRAPHICS] Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stackin g interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummer er rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic f luorinated beta -amino alcohols and alpha -amino acid derivatives, respecti vely.