Optically active polymer synthesis by Diels-Alder polymerization with chirally modified Lewis acid catalyst

A series of copolymers have been synthesized by Diels-Alder polymerization of bisdienophile monomer with bisdiene monomer. Bismaleimides (1) and bis(a lpha,beta-unsaturated ester)s (4) were prepared and used as bisdienophile m onomer. Furfuryl and butadienyl moieties were chosen as the diene part of t he 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 D iels-Alder polymerization was investigated. The use of enantiopure Lewis ac id catalysts (7-10) in the Diels-Alder polymerization of above monomers res ulted in the formation of optically active polymers having the asymmetric c arbons in their main chain.