Enzyme‐analogue built polymers, 13. On the introduction of amino‐ and boronic acid groups into chiral polymer cavities

With the aid of D‐glyceric acid as a template, an amino‐ and a boronic acid group, respectively, were introduced in a defined steric arrangement into polymers. For this, the monomer D‐N‐(4‐vinylphenyl)carbamoylethylenedioxy(4‐vinylphenyl)borane (1) was copolymerized into macroporous polymers under various conditions. The template D‐glyceric acid was split off from the polymer with 20% HCl in methanol. The specificity of the polymers obtained with one amino‐ and one boronic acid group, respectively, per cavity was derived from their ability to resolve racemic glyceric acid. Racemic resolution was also observed on equilibration of the polymers with D,L‐methyl glycerate and D,L‐glyceraldehyde.