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

BF3 함유 이분자형 키랄 살렌 촉매에 의한 고광학순도의 에피클로로히드린 합성

  • 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)
  • 이광연 (인하대학교 생명화학공학부) ;
  • 카테카라울 (인하대학교 생명화학공학부) ;
  • 김건중 (인하대학교 생명화학공학부)
  • Received : 2007.05.03
  • Accepted : 2007.06.26
  • Published : 2007.08.10

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

Acknowledgement

Supported by : 인하대학교

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