A chiral crown ether I was synthesized from (R)-1,1'-bi-2-naphthol. Chiral rotaxanes were prepared by end-capping of pseudorotaxanes consisting of 1 and secondary ammonium salts. An ammonium salt bearing terminal anthracene group gave stable pseudorotaxane. Chiral induction was observed during endcapping by radical conjugate addition of a bulky thiol to the pseudorotaxane bearing methacrylate group at the terminus.