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 Georgiadis, François Diederich

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

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
Volume56
Issue number10
StatePublished - 1991
Externally publishedYes

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Complexation
Alkaloids
Salts
Derivatives
Naproxen
Water
Binders
X rays
1,2,3,4-tetrahydroisoquinoline
naphthalene
2,3-bis(benzoyloxy)tartaric acid
diphenylmethane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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

In: Journal of Organic Chemistry, Vol. 56, No. 10, 1991, p. 3362-3369.

Research output: Contribution to journalArticle

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abstract = "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.",
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AB - 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.

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