Norbornen-5-yl carboxylic acid and norbornen-5-ylmethylsilyl ether-based beta -cyclodextrins (beta -CDs) containing up to three norbornene ester and up to five norbornene silyl ether units have been prepared from beta -CD and norbornen-5-carboxylic chloride and norbornen-5-ylmethyldichlorosilane, respectively. Oligomers (n = 2-4) were prepared therefrom using ring-opening metathesis polymerization (ROMP). Monomeric and oligomeric substituted beta -CDs were evaluated as chiral selectors in nonaqueous capillary zone electrophoresis using 35 mM sodium bicarbonate in N-methylformamide (NMF) as background electrolyte. Both monomeric and oligomeric norbornene ester- and norbornene silyl ether-type selectors showed good enantioresolution for dansylated (DNS-) amino acids using concentrations of the chiral selector of up to 4% w/v. A significant improvement in resolution was observed upon the introduction of up to five norbornene silyl ether units into a beta -CD molecule, whereas higher degrees of substitution with norbornen-5-yl-carboxyl groups read to a reduction in enantioresolution of DNS-amino acids. Thus, pentakis(norbornen-5-ylmethyihydroxysiloxyl)-beta -CD turned out to be superior to mono(norbornen-5-ylmethylhydroxysiloxyl)-beta -CD in terms of enantioresolution. Moreover, norbornene silyl ether-type selectors were found to be more efficient than norbornene ester-type selectors. Finally, oligomeric selectors were found to possess superior or at least comparable enantioselectivity in the separation of DNS- amino acids compared to the parent monomers. A maximum in enantioresolution was obtained with oligo(pentakis(norbornen-5-ylmethylhydroxysiloxyl)beta -CD).