A series of copolymers have been synthesized by Diels-Alder polymerization of bisdienophile monomer with bisdiene monomer. Bismaleimides (1) and bis(alpha,beta-unsaturated ester)s (4) were prepared and used as bisdienophile monomer. Furfuryl and butadienyl moieties were chosen as the diene part of the bisdiene monomers (2, 5). Repetitive Diels-Alder reactions between these monomers in the presence of Lewis acid catalyst yielded alternative Diels-Alder polymers (6, 12, 18, 15). On the basis of these results, asymmetric Diels-Alder polymerization was investigated. The use of enantiopure Lewis acid catalysts (7-10) in the Diels-Alder polymerization of above monomers resulted in the formation of optically active polymers having the asymmetric carbons in their main chain.