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化学学报
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化学学报 ›› 2005, Vol. 63 ›› Issue (12): 1136-1140. 上一篇    下一篇

研究简报

铑(II)催化重氮苄基膦酸酯与芳香亚胺的氮杂环丙烷化反应

李志成1 2，陈志勇2，胡文浩*2，余孝其1   

  1. (1四川大学化学学院 绿色化学与技术教育部重点实验室 成都 610064)
    (2中国科学院成都有机化学研究所 不对称合成与手性技术四川省重点实验室 成都 610041)
  • 投稿日期:2004-08-26 修回日期:2005-02-20 发布日期:2010-12-10
  • 通讯作者: 胡文浩

Rh(II) Catalyzed Aziridination of Diazobenzylphosphonate with Arylimines

LI Zhi-Cheng1,2, CHEN Zhi-Yong2, HU Wen-Hao*2, YU Xiao-Qi1   

  1. (1 Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064)
    (2 Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041)
  • Received:2004-08-26 Revised:2005-02-20 Published:2010-12-10

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被引次数

1

铑(II)催化重氮苄基膦酸酯与芳香亚胺反应, 一步合成氮杂环丙烷-2-膦酸酯. 该方法立体定向地得到唯一的反式构型产物, 反应历程是重氮化合物先与亚胺形成叶立德中间体, 然后发生自身环丙烷化反应.

关键词: 醋酸铑(II), 重氮苄基膦酸酯, 芳香亚胺, 反式氮杂环丙烷-2-膦酸酯

The reaction of diazobenzylphosphonate with arylimines catalyzed by dirhodium(II) complex stereospecifically gave trans-aziridines. The reaction pathway involved ylide intermediate in situ generated from diazobenzylphosphonate with an arylimine, which undergoes intramolecular ring closure to give aziridine-2-phosphonate. The products were characterized by 1H NMR, IR, MS spectra, elemental analysis and X-ray single crystal diffraction.

Key words: rhodium(II) acetate, diazobenzylphosphonate, arylimine, trans-aziridine-2-phosphonate