Based on highly stable chiral configuration of binaphthyls and behavior of extension/contraction of the dihedral angle between the two naphthalene rings in binaphthyl, we have designed two cyclophane enantiomers (R,R,R,R,R,R,R,R)-3 and (S,S,S,S,S,S,S,S)-3 containing eight chiral binaphthyl units by utilizing (R) and (S)-2,2'-diethynyl-1,1'-binaphthyl as hinges template, respectively. The synthetic procedure involved the multi steps reactions including the linking of meta-substituted benzene-bridge, removal and control introduction of protecting group, as well as intermolecular cross-coupling, etc. MS, IR, ¹H and ¹³C NMR as well as elemental analysis characterized intermediates and target compound 3. The specific rotations ([α]_D) of two isomers in CH₂Cl₂ are －911.8 and ＋908.6, and their circular dichroism (CD) spectra represented exactly mirror images of each other. These results reflected unambiguously enantiomeric relation between two optically pure isomers.

Key words: chirality, binaphthyl template, cyclophane, enantiomer, synthesis