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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (11): 1473-1476. 上一篇    下一篇

研究简报

新型手性N,N′-双支套索冠醚的合成及其应用

王成云*,1,2，汪大翚1，冷桃花2，俞庆森2   

  1. (1浙江大学环境工程研究所 杭州 310027)
    (2浙江大学化学系 杭州 310027)
  • 收稿日期:2005-04-09 修回日期:2005-05-24 发布日期:2005-10-30
  • 通讯作者: 王成云

Synthesis of New N,N′-Bichiral Lariat Crown Ethers and TheirApplication

WANG Cheng-Yun*,1,2,WANG Da-Hui1,LENG Tao-Hua2,YU Qing-Sen2   

  1. (1 Institute of Environmental Engineering, Zhejiang University, Hangzhou 310027)
    (2 Department of Chemistry, Zhejiang University, Hangzhou 310027)
  • Received:2005-04-09 Revised:2005-05-24 Published:2005-10-30
  • Contact: WANG Cheng-Yun

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(S)-苯丙氨醇和原氯乙酸三乙酯作用得到的手性酰胺醇和手性噁唑啉分别与1,7-二氮-12-冠-4反应, 得到了两种手性N,N′-双支套索冠醚N,N′-二[(S)-N-(1-羟甲基-2-苯基乙基)乙酰胺-2]-1,7-二氮-12-冠-4 (1a)和N,N′-二[(S)-4-苄基-噁唑啉-2-亚甲基]-1,7-二氮-12-冠-4 (1b). 前者应用于D/L-肉碱的手性分离; 后者的铜配合物用于重氮醋酸酯对烯烃的不对称环丙烷化反应.

关键词: 手性N,N′-双支套索冠醚, 不对称环丙烷化, 合成, D/L-肉碱, 手性分离

Two N,N′-bichiral lariat crown ethers, (S,S)-1,7-bis(4-benzyl-5-hydroxy-2-oxo-3-azapentyl)-1,7- diaza-12-crown-4 (1a) and (S,S)-1,7-bis(4-benzyloxazolin-2-yl-methyl)-1,7-diaza-12-crown-4 (1b), were obtained by alkylation of 1,7-diaza-12-crown-4 with (S)-(1-hydroxy-3-phenylprop-2-yl)-chloroacetamide or (S)-2-chloromethyl-4-benzyloxazoline, which were obtained by the reaction of (S)-2-amino-3-phenylpro- panol with triethyl orthochloroacetate. 1a was used successfully in the chiral separations of D/L-carnitine by capillary zone electrophoresis. Cu(II) complex of 1b was applied to the asymmetric cyclopropanation of 1,1-diphenylethylene with alkyl diazoace-tate.

Key words: synthesis, asymmetric cyclopropanation, D/L-carnitine, chiral separation, N,N′-bichiral lariat crown ether