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

DOI

10.3906/kim-1005-607

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.

Keywords

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

First Page

711

Last Page

718

Recommended Citation

KARADENİZ, LEMAN; KOZ, GAMZE; AYDIN, KADRİYE; and ASTLEY, STEPHEN THOMAS (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: Vol. 34: No. 5, Article 2. https://doi.org/10.3906/kim-1005-607
Available at: https://journals.tubitak.gov.tr/chem/vol34/iss5/2