chiral diepoxides, (2r,18r)-( $minus$ )- and (2s,18s)-( $plus$ )-5,6:14,15-dibenzo-1,2:18,19-diepoxy-4,7, 10,13, 16-pentaoxanonadeca-5,14-diene $left bracket$ (r,r)-( $minus$ )-1 and (s,s)-( $plus$ )-1 $right bracket$ , were synthesized enantiomerically and polymerized with a lewis acid and koh. all the polymers obtained were soluble in chcl//2 and consisted essentially of cyclic repeating units. the cd spectra of polymers from (r,r)-( $minus$ )-1 showed a positive cotton effect, while the polymers from (s,s)-( $plus$ )-1 presented a mirror image cd curve with a negative cotton effect. the polymers obtained with koh possessed higher stereoregularity than those with a lewis acid. the stereochemistries of polymers from (r,r)-( $minus$ )-and (s,s)-( $plus$ )-1 with koh were poly $left bracket$ (r,r)-dibenzo-19-crown-6 $right bracket$ and poly $left bracket$ (s,s)-dibenzo-19-crown-6$rb, respectively polymers 2 and 8 obtained from (s,s)-( $plus$ )-1 with sncl//4 and koh, respectively, formed the host-guest complex dominantly with the d-isomers of phenylglycine, phenylalanine, and methionine methyl esters. the optical purities of guests extracted by the both polymers were as low as values ranging from 0.5 to 5.4. for every host-guest system, the chiral recognition property of polymer 8 was higher-than that of polymer 2. (author abstract) 11 refs