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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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Article information


Submitted
18 Oct 2007
Accepted
20 Nov 2007
First published
28 Nov 2007

Chem. Commun., 2008, 561-563
Article type
Communication

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, 561
DOI: 10.1039/B716105K

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