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Publication 71  

  1. Towards the stereoselective synthesis of inherently chiral pseudorotaxanes
    Pierre Mobian, Natalie Banerji, Gérald Bernardinelli, Jérôme Lacour
    Org. Biomol. Chem. 2006, 4, 224-231

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 PF6analogues (× 7.3). A general lack of diastereoselectivity (de ≤ 8%) was unfortunately observed.

DOI: 10.1039/b513562a 

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