Volume 22, Issue 39
Heterocyclic Compounds
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ChemInform Abstract: 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.

T. M. GEORGIADIS

T. M. GEORGIADIS

Dep. Chem. Biochem., Univ. California, Los Angeles, CA 90024-1569, USA

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M. M. GEORGIADIS

M. M. GEORGIADIS

Dep. Chem. Biochem., Univ. California, Los Angeles, CA 90024-1569, USA

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F. DIEDERICH

F. DIEDERICH

Dep. Chem. Biochem., Univ. California, Los Angeles, CA 90024-1569, USA

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First published: October 1, 1991

Abstract

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ChemInform Abstract

Cyclization of the chiral naphthalenyltetrahydroisoquinoline derivative (I) with the bis(hydroxyphenyl)piperidine derivative (II) yields the optically active macrocycle (III). After reduction of the two N-acetyl groups in (III) with BH3×THF and subsequent quaternization of the two tertiary amino groups with ethyl iodide and ion exchange of iodide to chloride, a macrocyclic dication is obtained which shows modest chiral recognition in the inclusion complexation of naproxen derivatives.

chemical structure image

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