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Synthesis of Optically pure Epichlorohydrine using Dimeric Chiral Salen Catalyst Containing BF3  

Lee, Kwang-Yeon (Th School of Chemical Engineering and Biotechnology, Inha University)
Rahul, B. Kawthekar (Th School of Chemical Engineering and Biotechnology, Inha University)
Kim, Geon-Joong (Th School of Chemical Engineering and Biotechnology, Inha University)
Publication Information
Applied Chemistry for Engineering / v.18, no.4, 2007 , pp. 330-336 More about this Journal
Abstract
In this study, new dinuclear chiral Co (salen) complexes bearing $BF_3$ have been synthesized and their properties as the asymmetric catalyst have been examined. The NMR, UV and ESCA analyses were performed to determine the structure of synthesized catalysts. Their catalytic activity and selectivity have been demonstrated for the asymmetric ring opening of various terminal epoxides by hydrolytic kinetic resolution technology. The easily prepared dimeric complexes exhibited very high enantioselectivity for the asymmetric ring opening of epoxides with $H_2O$ nucleophile, providing enantiomerically enriched terminal epoxides (> 99 %ee). The dimeric structured chiral salen showed remakablely enhanced reactivity and may be employed substantially lower loadings than its monomeric analogues, and in addition no racemization happened during the separation of product epoxides. 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; enantioselectivity; optical isomer; hydrolytic kinetic resolution;
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