Enantiomerically pure 1-(2-methoxy-1-naphthyl) and 1-(2-methylthio-1-naphthyl)isoquinoline: two new axially chiral N-O and N-S ligands for asymmetric catalysis

The synthesis and resolution of 1-(2-methoxy-1-naphthyl)isoquinoline and 1-(2-methylthio-1-naphthyl)isoquinoline is reported. These ligands were assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate. Enantioselectivity up to 68% was obtained.