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Keywords:

  • Bis(2-oxazolines);
  • Chelating ligands;
  • Zinc complexes;
  • Catalysis

Abstract

Dinitriles (57, 12, 13) react with enantiomerically pure β-amino alcohols (811,17) under zinc chloride catalysis to give optically active C2-symmetric bis(oxazolines). 1,2-Bis(2-oxazolin-2-yl)benzenes 1ae are obtained under mild reaction conditions. 1H-NMR spectroscopy indicates the formation of 1:1 complexes 23 of these compounds with ZnCl2. The energy required for a conformational interconversion of zinc dichloride complex 23e was determined by variable-temperature 1H-NMR studies. An X-ray structure analysis was performed with the substituted [1,2-bis(2-oxazolinyl)benzene]zinc dichloride complex 23a.