Four pyridyl substituted helically chiral poly(methacrylate)s poly-1-poly-4 were oxidized with m-CPBA, yielding four pyridyl N-oxide substituted polymers poly-5-poly-8. Poly[(3-pyridyl N-oxide)-dibenzosuberyl methacrylate] poly(3PyDBSMA-NO) poly-5 was found to be quantitatively oxidized and showed a stable helical conformation. It was an active organocatalyst in the asymmetric allylation of benzaldehyde with allyltrichlorosilane.