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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (04): 601-605. 上一篇    下一篇

研究论文

有机锂试剂对二茂铁亚胺的不对称加成反应

张慧卿; 袁 浩 ; 周智明*   

  1. (北京理工大学化工与环境学院 北京 100081)
  • 收稿日期:2008-05-05 修回日期:2008-10-17 发布日期:2009-04-20
  • 通讯作者: 周智明

Asymmetric Addition of Organolithium Reagents to Ferrocenylimines

Zhang, Huiqing; Yuan, Hao ; Zhou, Zhiming*   

  1. (School of Chemical Engineering & the Environment, Beijing Institute of Technology, Beijing 100081)
  • Received:2008-05-05 Revised:2008-10-17 Published:2009-04-20
  • Contact: Zhou, Zhiming

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研究了利用(－)-sparteine辅助的有机锂试剂对非手性二茂铁亚胺的对映选择性加成和对衍生于廉价的苯乙胺的手性二茂铁亚胺的非对映选择性加成反应. 对亚胺结构和实验条件对反应的影响进行了深入研究. 在有机锂试剂对非手性二茂铁亚胺的对映异构体选择性加成中得到了中等的对映选择性, 对衍生于(R)-苯乙胺的手性二茂铁亚胺的非对映选择性加成反应, 路易斯酸BF3•OEt2的添加对反应非常有利, 得到了非常好的非对映选择性.

关键词: 二茂铁亚胺, (－)-sparteine, 路易斯酸, 不对称加成

The (－)-sparteine-mediated enantioselective addition of organolithium compounds to achiral ferrocenylimines and diastereoselective addition of organolithium reagents to chiral ferrocenyl imines de-rived from inexpensive (R)- and (S)-1-phenylethylamines were carried out. The influence of the imine struc-ture, as well as the effect of experimental conditions on the reaction was studied. Modest enantiomeric ex-cess was obtained with the achiral imines. And high diastereoselectivity was achieved with the chiral imine derived from (R)-(＋)-1-phenylethylamine in the presence of the Lewis acid BF3•OEt2.

Key words: ferrocenylimine, (－)-sparteine, asymmetric addition, Lewis acid