Asymmetric anionic polymerization of 1-phenyldibenzosuberyl methacrylate [5-phenyldibenzosuberan-5-yl methacrylate, 5-phenyl-10,11-dihydrodibenzo[a,d]cyclohepten-5-yl methacrylate] (1), and 1-(2-pyridyl)dibenzosuberyl meth-acrylate [5-(2-pyridyl)dibenzosuberan-5-yl methacrylate, 5-(2-pyridyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-yl methacrylate] (2) was carried out using complexes of N,N′-diphenylethylenediamine monolithium amide with (−)-sparteine (Sp), (+)-1-(2-pyrrolidinylmethyl)pyrrolidine (PMP), and (+)-2,3-dimethoxy-1,4-bis(dimethylamino)butane (DDB) in toluene at −78°C. The polymers of 1 quantitatively obtained with the three complexes were highly isotactic and showed high optical activity ([α]365+1670−1780°, [α]D480°) and intense circular dichroism absorptions based on one-handed helical conformation of main chain. In contrast, 2 gave one-handed helical polymers only by the polymerization with the Sp and PMP complexes. The polymerization of 2 with the DDB complex was sluggish. Monomers 1 and 2 showed higher resistance against methanolysis compared with triphenylmethyl methacrylate and diphenyl-2-pyridylmethyl methacrylate, respectively. The obtained optically active polymers resolved several racemic compounds.