Polymeric chiral crown ethers, 5. Synthesis of polymers by cyclopolymerization of divinyl ethers containing moieties deriving from L ‐tartaric acid, and the chiral recognition toward amino acids

The synthesis of polymers with chiral crown ether units containing moieties deriving from L‐tartaric acid via cyclopolymerization of divinyl ethers was studied. 1,4‐Di‐O‐benzyl‐ and 1,4‐di‐O‐trityl‐2,3‐bis{O‐[2‐(2‐vinyloxyethoxy)ethyl]}‐L‐threitol (1a and 1b) were polymerized with cationic catalysts to produce polymers (2a and 2b) consisting of only cyclic constitutional units. The trityl groups in polymer 2b were easily cleaved by hydrogen chloride to form a water‐soluble, chiral polymer. Polymer 2b was found to complex predominantly with the L‐enantiomer of ester salts of phenylglycine, phenylalanine, valine, and methionine in the same way as a chiral polymer incorporating 1,3:4,6‐di‐O‐benzylidene‐D‐mannitol moieties.