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, cilt.34, ss.711-718, 2010 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 34 Konu: 5
  • Basım Tarihi: 2010
  • Doi Numarası: 10.3906/kim-1005-607
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Sayfa Sayıları: ss.711-718

Özet

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.