Synthesis and Enantiomer Recognition of Dipodands and Crown Ethers Containing the 2,3:6,7-Dibenzobicyclo[3.3.1]nona-2,6-diene Residue as the Chiral Subunit

Five new optically active crown ethers and six optically active dipodands are reported. The crown ethers were synthesized by using (+)-(1S,4R,5S,8R)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-diol and (+)-(1S,4R,5S,8R)-4,8-bis(hydroxymethyl)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene as a chiral subunit and the dipodands contained the 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene residue as a chiral anchor group. The enantiomer recognition behaviour of these compounds was evaluated by the enantiomer differential transport of methyl (±)-phenylglycinate and (±)-1,2-diphenylethylamine hydrochloride through bulk liquid membrane.