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Acta Chimica Sinica ›› 2005, Vol. 63 ›› Issue (12): 1136-1140. Previous Articles     Next Articles

Reports

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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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