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Enantioselective Epoxide Synthesis on the Chiral Salen Catalyst having a Transitional Metal Salt  

Guo, Xiao-Feng (Department of Chemical Engineering, Inha University)
Kawthekar, Rahul B. (Department of Chemical Engineering, Inha University)
Kim, Geon-Joong (Department of Chemical Engineering, Inha University)
Publication Information
Korean Chemical Engineering Research / v.46, no.4, 2008 , pp. 769-776 More about this Journal
Abstract
The stereoselective synthesis of chiral terminal epoxide is of immense interest due to their utility as versatile starting materials as well as chiral intermediates. In this study, new chiral Co(salen) complexes bearing cobalt(II) chloride, iron(III) chloride and zinc(II) nitrate have been synthesized and characterized. The mass and EXAFS spectra provided the direct evidence of formation of complex. Their catalytic activity and selectivity have been demonstrated for the asymmetric ring opening of terminal epoxides such as styrene oxide and phenylglycidylether by hydrolytic kinetic resolution technology and for the synthesis of glycidyl buthylate. The easily prepared complexes exhibited very high enantioselectivity for the asymmetric ring opening of epoxides with $H_2O$ nucleophile, providing enantiomerically enriched terminal epoxides (>99% ee). The newly synthesized chiral salen showed remakablely enhanced reactivity with substantially low loadings. The system described in this work is very efficient for the sinthesis of chiral epoxide and 1,2-diol intermediates.
Keywords
Chiral Salen; Asymmetric Ring Opening; Epoxide; Enantioselectivity; Optical Isomer; Hydrolytic Kinetic Resolution;
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