Issue 5, 2008
From the journal:

Chemical Communications

Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids†

Jonathan Clayden,*a   Lluís Vallverdú,‡a   James Claytona  and  Madeleine Helliwella  

* Corresponding authors

a School of Chemistry, University of Manchester, Oxford Road, Manchester, UK
E-mail: clayden@man.ac.uk

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

DOI
https://doi.org/10.1039/B716105K
Article type
Communication
Submitted
18 Oct 2007
Accepted
20 Nov 2007
First published
28 Nov 2007

Chem. Commun., 2008, 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, 561 DOI: 10.1039/B716105K

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