Chiral polymer materials: a protective group approach to ascertain asymmetric inductions in the backbone of 1,2-disubstituted vinyl type polymers by chiral template mediated polymerization

A synthetic methodology is described for unequivocally establishing asymmetric induction in the backbone of copolymers based on 1,2-disubstituted olefins and 1-substituted olefins. For this purpose functional styrene monomers (e.g. 4-vinyl benzaldehyde and 4-vinyl boronic acid) were derivatized with chiral auxiliaries, such as R(+)-1-phenyl ethyl amine and diethyl-L-tartrate, which act as protecting groups for the functional groups of the styrene monomers. Copolymerization with maleimide derivatives followed by the removal of the chiral protecting groups produced the appropriate functional copolymers. Spectroscopic techniques were used to confirm quantitative deprotection had occurred and chiroptical techniques were used to ascertain asymmetric inductions in the polymer backbone