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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (03): 341-345. 上一篇    下一篇

研究论文

季铵盐中N-手性在不对称烷基化反应中的作用研究

鲁军1,2，廖霞俐1,2，陈晓珍1，王淳*,1   

  1. (1中国科学院成都生物研究所天然产物中心 成都 610041)
    (2中国科学院研究生院 北京 100049)
  • 收稿日期:2010-04-07 修回日期:2010-09-09 发布日期:2010-10-27
  • 通讯作者: 王淳 E-mail:wangchun@cib.ac.cn
  • 基金资助:

    N手性季铵盐的合成

Significance of N-Stereogenic Centre in Quaternary Ammonium Salts in Asymmetric Alkylation

Lu Jun1,2 Liao Xiali1,2 Chen Xiaoz-hen1 Wang Chun*,1   

  1. (1 Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041)
    (2 Graduate School of Chinese Academy of Sciences, Beijing 100049)
  • Received:2010-04-07 Revised:2010-09-09 Published:2010-10-27
  • Contact: Chun Wang E-mail:wangchun@cib.ac.cn

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为了探明手性季铵盐中N-手性在不对称烷基化反应中的作用, 从天然氨基酸出发合成了4个仅含C-手性的季铵盐, 将它们与4个同时含有C-和N-手性的季铵盐用于催化二苯亚胺甘氨酸叔丁酯的不对称烷基化反应, 通过对烷基化产物的ee值进行比较, 结果表明简单的链状季铵盐中的N-手性不能对烷基化产物的ee值产生明显影响.

关键词: N-手性季铵盐, 不对称催化, 氨基酸, 烷基化

To elucidate the asymmetric inductive effect of the N-stereogenic centre in quaternary ammonium salts, four quaternary ammonium salts with C-chiral centre were synthesized from amino acids. These salts together with four previously synthesized salts containing both N- and C-chiral centres, were applied as asymmetric phase-transfer catalysts in the enantioselective alkylation of N-(diphenylmethylene)-glycine tert-butyl ester with benzyl bromide. The relationship be-tween the ee values of products and the structures of catalysts indicated that the N-stereogenic centre alone showed no significant effect on the enantioselectivity of alkylation.

Key words: N-stereogenic quaternary ammonium salt, asymmetric catalysis, amino acid, alkylation