Co(III) catalysed asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives: reversal of enantioselectivity and rate acceleration on addition of AlCl3
Articles > Article · 2010
Authors: Leman ALKAN, Gamze Koz, Kadriye Aydın, Stephen Thomas ASTLEY
TURKISH JOURNAL OF CHEMISTRY, Journal Indexed in SCI Expanded, International, 2010, vol 34, pp 711-718
DOI: 10.3906/kim-1005-607
Summary
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.