Yamamoto coupling polymerizations of 2,3-dihalido-N-substituted maleimides (DXRMI) were carried out using nickel catalysts. In addition, coupling reactions of 2,3-dihalido-N-cyclohexylmaleimide (DXCHMI) were performed with nickel complexes in the presence of directly coupled chiral bisoxazolines (R′box) to give optically active poly(N-substituted maleimide-2,3-diyl)s [poly(RMI)s] (specific rotation [α]₄₃₅ = +6.0 to −34.6°). Polymers with number-average molecular weights (M_n) ranging from 270 to 36200 were obtained in 17% to quantitative yields. Poly(N-cyclohexylmaleimide-2,3-diyl) [poly(CHMI)] formed with [Ni(cod)₂]–R′box exhibited the largest absolute value, [α]₄₃₅ = −34.6°.