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高等学校化学研究 ›› 2011, Vol. 27 ›› Issue (1): 45-48.

• Articles • 上一篇    下一篇

Enantioselective Iodolactonizations of (E)- and (Z)-5-Substituted-4-pentenoic Acid Derivatives Mediated by Chiral Salen-Co(II) Complex

NING Zhao-lun1,2, DING Jin-ying1, JIN Ri-zhe1, KANG Chuan-qing1, CHENG Yan-qin1 and GAO Lian-xun1*   

  1. 1. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
    2. Graduate School of Chinese Academy of Sciences, Beijing 100049, P. R. China
  • 收稿日期:2010-05-19 修回日期:2010-06-08 出版日期:2011-01-25 发布日期:2011-01-04
  • 通讯作者: GAO Lian-xun E-mail:lxgao@ciac.jl.cn

Enantioselective Iodolactonizations of (E)- and (Z)-5-Substituted-4-pentenoic Acid Derivatives Mediated by Chiral Salen-Co(II) Complex

NING Zhao-lun1,2, DING Jin-ying1, JIN Ri-zhe1, KANG Chuan-qing1, CHENG Yan-qin1 and GAO Lian-xun1*   

  1. 1. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
    2. Graduate School of Chinese Academy of Sciences, Beijing 100049, P. R. China
  • Received:2010-05-19 Revised:2010-06-08 Online:2011-01-25 Published:2011-01-04
  • Contact: GAO Lian-xun E-mail:lxgao@ciac.jl.cn

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摘要： A number of salen-metal complexes were prepared and their enantioselective catalytic properties toward the asymmetric iodolactonization of (E)- and (Z)-5-substituted-4-pentenoic acid derivatives were investigated. The catalyst system based on salen-Co(II) complex exhibited moderate to good enantioselectivity with the e.e. value ranging from 53% to 74%, as well as high regioselectivity of δ- vs. γ-iodolactones. The salen-Co(II) complex showed the highest enantioselectivity on the asymmetric iodolactonizations of (Z)-5-substituted-4-pentenoic acid derivatives among these reagent-controlled iodolactonization protocols known so far.

关键词: Asymmetric catalysis, Salen-complex, Iodolactonization

Abstract: A number of salen-metal complexes were prepared and their enantioselective catalytic properties toward the asymmetric iodolactonization of (E)- and (Z)-5-substituted-4-pentenoic acid derivatives were investigated. The catalyst system based on salen-Co(II) complex exhibited moderate to good enantioselectivity with the e.e. value ranging from 53% to 74%, as well as high regioselectivity of δ- vs. γ-iodolactones. The salen-Co(II) complex showed the highest enantioselectivity on the asymmetric iodolactonizations of (Z)-5-substituted-4-pentenoic acid derivatives among these reagent-controlled iodolactonization protocols known so far.

Key words: Asymmetric catalysis, Salen-complex, Iodolactonization