Organocatalytic formation of optically active polymers: enantioselective aldol reaction of aldehyde-containing copolymers in the presence of L-proline

Monomers containing benzaldehyde units were synthesized by esterification of 4-hydroxybenzaldehyde and 4-(2-hydroxyethoxy)benzaldehyde with methacryloyl chloride. These monomers were copolymerized free radically with N-isopropylacrylamide using 2,2-azobis(2-methylpropionitrile) as an initiator. The monomers and copolymers, respectively, were modified with acetone in an organocatalytic aldol reaction in the presence of l-proline to induce stereogenic centers. The aldol condensates were characterized by their optical rotatory power. (c) 2014 Society of Chemical Industry