Stereospecific radical polymerization of optically active (S)-N-(2-hydroxy-1-phenylethyl) methacrylamide catalyzed by Lewis acids.

Highlights: [•] Stereospecific radical polymerization of optically active (S)-HPEMA was realized. [•] A catalytic amount of the Lewis acid is enough to control the stereoregularity. [•] Solvents strongly influence the effect of Lewis acids on the tacticity of the polymer. [•] The polymerization in n-BuOH in the presence of La(OTf)3 shows the highest isotacticity. [•] The mechanism of stereocontrol was analyzed based on Lewis acid-monomer interaction. [Copyright &y& Elsevier]