Co(III) catalysed asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives: reversal of enantioselectivity and rate acceleration on addition of AlCl3

Karadeniz L. , Koz G., Aydın K., Astley S. T.

TURKISH JOURNAL OF CHEMISTRY, vol.34, no.5, pp.711-718, 2010 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 5
  • Publication Date: 2010
  • Doi Number: 10.3906/kim-1005-607
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.711-718

Abstract

Using asymmetric Cobalt(III) salen catalysts, the ring-opening of epichlorohydrin by 2,3-dihydroxybenzaldehyde and 2,4-dihydroxybenzaldehyde was found to occur at the phenolic groups most distant from the aldehydic group. Switching catalysts afforded a reversal in enantioselectivity. For 2,3-dihydroxybenzaldehyde and salicylaldehyde, addition of AlCl3 to the reaction mixture led to an increase in reaction rate without any decrease in product enantiopurity.