Co(III) catalysed asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives: reversal of enantioselectivity and rate acceleration on addition of $AICl_3$

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 $AICI _3$to the reaction mixture led to an increase in reaction rate without any decrease in product enantiopurity.