SYNTHESIS AND COMPLEXATION PROPERTIES OF A WATER-SOLUBLE OPTICALLY-ACTIVE CYCLOPHANE INCORPORATING A 4-NAPHTHYL-1,2,3,4-TETRAHYDROISOQUINOLINE UNIT AS A CHIRAL SPACER

The unnatural alkaloid 6-methoxy-4-[2-(6-methoxynaphthalenyl)]-1,2,3,4-tetrahydroisoquinoline (5) was prepared as a chiral spacer for optically active cyclophane receptors. Optical resolution of the building block was accomplished through diastereomeric salt formation with dibenzoyltartaric acid. The S configuration was assigned by X-ray crystallographic methods to the hydrochloride salt of (-)-5. Starting from enantiomerically pure 5, the optically active cyclophanes (R)- and (S)-4 were prepared. These cycophanes, in which the chiral alkaloid spacer is bridged to an achiral diphenylmethane unit, are efficient binders of napthalene derivatives in D2O/CD3OD (60:40, v/v) and show a modest degree of chiral recognition in the inclusion complexation of naproxen derivatives.