Co(III) catalysed asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives: reversal of enantioselectivity and rate acceleration on addition of AlCl_3

Authors

LEMAN KARADENİZ
GAMZE KOZ
KADRİYE AYDIN
STEPHEN THOMAS ASTLEY

Abstract

Using asymmetric Cobalt(III) salen catalysts, the ring-opening of epichlorohydrin by 2,3-dihydroxybenzal- dehyde 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 AlCl_3 to the reaction mixture led to an increase in reaction rate without any decrease in product enantiopurity.

DOI

10.3906/kim-1005-607

Keywords

Asymmetric catalysis; salicylaldehyde; Co(III) salen; aryloxy alcohols; epoxide ring-opening

First Page

711

Last Page

718

Recommended Citation

KARADENİZ, L, KOZ, G, AYDIN, K, & ASTLEY, S. T (2010). Co(III) catalysed asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives: reversal of enantioselectivity and rate acceleration on addition of AlCl_3. Turkish Journal of Chemistry 34 (5): 711-718. https://doi.org/10.3906/kim-1005-607