The diastereoselective nucleophilic addition of alkyllithium to N-alkylidene-α-naphthylethylamine
was carried out. In the presence of Lewis acids or Lewis bases, organolithiums reacted smoothly
with imines to give the corresponding amines in high stereoselectivity (up to 100% de). Furthermore,
the resulting optically active amines were found to be useful for asymmetric reactions as chiral
ligands.