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

Taxiarchis M. Georgiadis, Millie M. Georgiadis, François Diederich

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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 cyclophanes, in which the chiral alkaloid spacer is bridged to an achiral diphenylmethane unit, are efficient binders of naphthalene derivatives in D2O/CD3OD (60:40, v/v) and show a modest degree of chiral recognition in the inclusion complexation of naproxen derivatives.

Original languageEnglish (US)
Pages (from-to)3362-3369
Number of pages8
JournalJournal of Organic Chemistry
Issue number10
StatePublished - May 1 1991


ASJC Scopus subject areas

  • Organic Chemistry

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