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

Jonathan Clayden*, Lluís Vallverdú, James Clayton, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)561-563
Number of pages3
JournalChemical Communications
Volume8
Issue number5
Early online date28 Nov 2007
DOIs
Publication statusPublished - 7 Feb 2008

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