Syntheses and Reactions of Optically Active Polymers. I. Syntheses and Polymerizations of N-Vinylbenzyl- l -amino Acid Derivatives

N-Vinylbenzyl-l-amino acids were synthesized by the reaction of l-amino acids with formylstyrenes and the subsequent reduction of the condensation products with sodium borohydride. The procedure was performed without protection of the various functional groups of amino acids and racemization was not accompanied by the above process. The method is useful for the synthesis of optically active vinyl monomers containing various amino acids with their intact functionality. As a representative l-amino acid, a variety of N-vinylbenzyl-l-leucine derivatives such as N-methyl-l-leucine, l-leucine ethyl ester, l-leucinol and N-formyl-l-leucine ethyl ester were prepared by means of chemical transformation. These optically active monomers of leucine derivatives were polymerized to optically active polymers.