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.
Asymmetric catalysis; salicylaldehyde; Co(III) salen; aryloxy alcohols; epoxide ring-opening
KARADENİZ, LEMAN; KOZ, GAMZE; AYDIN, KADRİYE; and ASTLEY, STEPHEN THOMAS
"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:
5, Article 2.
Available at: https://journals.tubitak.gov.tr/chem/vol34/iss5/2