Asymmetric anionic polymerizations of achiral N-diphenylmethylitaconimide (DPII) were performed with chiral ligand - organometal complexes in toluene. The obtained poly(DPII)s exhibited molecular weights of 1.5 x 10(3) to 6.3 x 10(3) and specific rotation ([alpha](435)(25)) between +7.5 to -18.4degrees (THF). The chirality of polymer was significantly affected by the organometals and chiral ligands. The poly(DPII) obtained with (4S)-2,2'-(1-ethylpropylidene)bis(4-benzyl-4,5-dihydrooxazole) (Bnbox) / n-butyllithium (n-BuLi) exhibited the highest specific rotation (-18.4degrees). The optical activities of the poly(DPII)s were attributed to configurational chirality of the main chain more than conformational chirality, judged from NMR, circular dichroism (CD) and GPC analyses using UV and polarimetric detectors.