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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (04): 568-572. 上一篇    下一篇

研究简报

在不对称氮杂环丙烷化中双噁唑啉配位空间大小对对映选择性的影响

马琳鸽，杜大明，许家喜*   

  1. (北京大学化学与分子工程学院 生物有机与分子工程教育部重点实验室 北京 100871)
  • 收稿日期:2005-07-11 修回日期:2005-10-31 发布日期:2006-03-31
  • 通讯作者: 许家喜

Effect of Chelate Size of Bisoxazolines on the Enantioselectivity of the Asymmetric Aziridination

MA Lin-Ge,DU Da-Ming,XU Jia-Xi*   

  1. (Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education,
    College of Chemistry and Molecular Engineering, Peking University, Beijing 100871)
  • Received:2005-07-11 Revised:2005-10-31 Published:2006-03-31
  • Contact: XU Jia-Xi

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手性双噁唑啉是在不对称催化中广泛应用的一类重要的配体. 合成了一系列具有刚性骨架和不同配位空间的手性双噁唑啉配体, 并研究了在不对称氮杂环丙烷化反应中对对映选择性的影响, 结果表明通过调节配位空间的大小不仅可以改变对映选择性, 甚至还可以彻底改变对映面选择性. 研究结果还表明除通过改变配体手性中心的构型, 调节配体配位空间也可以改变催化剂的对映面选择性.

关键词: 配体, 配位空间大小, 不对称氮杂环丙烷化, 对映选择性, 双噁唑啉

Chiral bisoxazolines have been widely applied ligands to asymmetric catalysis and a series of optically active bisoxazolines with rigid backbones and different chelate sizes were synthesized. The effect of their chelate sizes on the enantioselectivity was investigated in the asymmetric aziridination. The results indicate that tuning chelate size can not only change the enantioselectivity, but also change the enantiofacial se-lectivity completely.

Key words: chelate size, asymmetric aziridination, ligand, enantioselectivity, bisoxazoline