Asymmetric Addition of Alkyllithium to Chiral Imines: alpha-Naphthylethyl Group as a Chiral Auxiliary.

The diastereoselective nucleophilic addition of alkyllithium to N-alkylidene-alpha-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.