A cationic gold(I)/axially chiral biaryl bis(phosphine) complex has been employed to catalyze the asym. dearomatization reactions of 1-aminonaphthalene derivs. through a C-C bond-forming reaction with electron-rich heterocycles as the nucleophiles. These reactions afford pentacyclic heterocycles in good yields with moderate enantiomeric excess (ee) values. [on SciFinder(R)]