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.
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.