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Issue 5, 2008
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Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids

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Abstract

Tertiary diamides of xanthene-1,8-dicarboxylic acid and biphenyl-2,2′-dicarboxylic acid exhibit a thermodynamic preference for anti stereochemistry which is inverted in the presence of Ti- or Sn-based Lewis acids, allowing interconversion between kinetically stable syn and anti diastereoisomeric atropisomers.

Graphical abstract: Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids

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Publication details

The article was received on 18 Oct 2007, accepted on 20 Nov 2007 and first published on 28 Nov 2007


Article type: Communication
DOI: 10.1039/B716105K
Citation: Chem. Commun., 2008,0, 561-563
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    Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids

    J. Clayden, L. Vallverdú, J. Clayton and M. Helliwell, Chem. Commun., 2008, 0, 561
    DOI: 10.1039/B716105K

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