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Asymmetric Ring Opening Reaction of Racemic Epoxides by Polymeric Chiral Salen Catalyst containing Metal Salts  

Lee, Kwang Yeon (Department of Chemical Engineering, Inha University)
Rahul, B. Kawthekar (Department of Chemical Engineering, Inha University)
Kim, Geon-Joong (Department of Chemical Engineering, Inha University)
Publication Information
Applied Chemistry for Engineering / v.18, no.6, 2007 , pp. 562-567 More about this Journal
Abstract
The stereoselective synthesis of chiral terminal epoxide is of immense academic and industrial interest due to their use as versatile starting materials as well as chiral intermediates. In this study, new polymeric chiral Co(salen) complexes bearing tallium (III)chloride and iron (III)chloride (ferric chloride) have been synthesized and characterized. Their catalytic activity and selectivity have been demonstrated for the asymmetric ring opening of various terminal epoxides using water and phenol derivatives as nucleophiles. The easily prepared polymeric complexes exhibited very high enantioselectivity for the asymmetric ring opening of epoxides with $H_2O$ and phenol nucleophiles, providing enantiomerically enriched terminal epoxides (> 98% ee). The system described in this work is very efficient for the synthesis of chiral epoxide, 1,2-diol and ${\alpha}$-aryloxy alcohol intermediates.
Keywords
chiral polymeric salen; chiral intermediates; terminal epoxides; kinetic resolution; asymmetric catalysis;
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