Issue 2, 2006
From the journal:

Organic & Biomolecular Chemistry

Towards the stereoselective synthesis of inherently chiral pseudorotaxanes†

Pierre Mobian,a   Natalie Banerji,a   Gérald Bernardinellib  and  Jérôme Lacour*a  

* Corresponding authors

a Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, Geneva 4, Switzerland
E-mail: jerome.lacour@chiorg.unige.ch
Fax: +41 22 328 7396

b Laboratory of Crystallography, University of Geneva, Quai Ernest Ansermet 24, Genève 4, Switzerland

Abstract

Herein is reported an investigation towards the stereoselective synthesis of inherently chiral pseudorotaxanes. Chiral ammonium threads were readily prepared in five steps from racemic or enantiopure (M or P) salts of di-n-propyl-1,13-dimethoxyquinacridinium cation. Their self-assembly with DB24C8 or disymmetrically oriented DB24C8F6 rings formed pseudorotaxanes as shown by 1H and 19F NMR spectroscopy as well as MS measurements. A determination of the association constants (Ka) was afforded. The crucial role played by the ammonium counter-ion in the threading process was further demonstrated as salts of TRISPHAT (tris(tetrachlorobenzenediolato)phosphate(V)) anion were quite more effective than their PF6− analogues (× 7.3). A general lack of diastereoselectivity (de ≤ 8%) was unfortunately observed.

Graphical abstract: Towards the stereoselective synthesis of inherently chiral pseudorotaxanes

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Article information

DOI
https://doi.org/10.1039/B513562A
Article type
Paper
Submitted
26 Sep 2005
Accepted
14 Nov 2005
First published
07 Dec 2005

Org. Biomol. Chem., 2006,4, 224-231

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Towards the stereoselective synthesis of inherently chiral pseudorotaxanes

P. Mobian, N. Banerji, G. Bernardinelli and J. Lacour, Org. Biomol. Chem., 2006, 4, 224 DOI: 10.1039/B513562A

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