Conformational switching between diastereoisomeric atropisomers of arenedicarboxamides induced by complexation with Lewis acids.
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.
Clayden
Jonathan
J
School of Chemistry, University of Manchester, Oxford Road, Manchester, UK. clayden@man.ac.uk
Vallverdú
Lluís
L
Clayton
James
J
Helliwell
Madeleine
M
D000143:Acids / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003998:Dicarboxylic Acids / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013816:Thermodynamics; D014001:Tin / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry*
D000143:Acids; D000577:Amides; D003998:Dicarboxylic Acids; D014001:Tin; D014025:Titanium