Homopolymerization and copolymerization of N-substituted maleimides with chiral anionic initiators

Novel optically active anionic initiators bearing a chiral oxazole substituent on the fluorene ring, ( S )-1-(9H-fluoren-2-yl)-4-isopropyl-4,5-dihydrooxazole lithium (Li-( S )-1-FIDH) and ( S )-2-(9H-fluoren-2-yl)-4-isopropyl-4,5-dihydrooxazole lithium (Li-( S )-2-FIDH), were prepared. Anionic homopolymerizations of achiral N -substituted maleimide (RMI) with the chiral initiators were investigated. The optically active polymers obtained were attributed to asymmetric induction of the chiral initiators. The very crowded chiral initiator Li-( S )-1-FIDH was found to play a better asymmetric induction role in the polymers than Li-( S )-2-FIDH. Anionic copolymerization of ( R )-(+)- N -1-phenylethyl maleimide and optically inactive RMI with Li-( S )-1-FIDH were also studied. © 2014 Society of Chemical Industry