| 季铵盐中N-手性在不对称烷基化反应中的作用研究 |
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| 引用本文： | 鲁军,廖霞俐,陈晓珍,王淳.季铵盐中N-手性在不对称烷基化反应中的作用研究[J].有机化学,2011,31(3). |
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| 作者姓名： | 鲁军 廖霞俐 陈晓珍 王淳 |
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| 作者单位： | 1. 中国科学院成都生物研究所天然产物中心,成都,610041;中国科学院研究生院,北京,100049
2. 中国科学院成都生物研究所天然产物中心,成都,610041 |
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| 摘 要： | 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.
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| 关 键 词： | N-手性季铵盐 不对称催化 氨基酸 烷基化 |
Significance of N-Stereogenic Centre in Quaternary Ammonium Salts in Asymmetric Alkylation |
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| Lu Jun,Liao Xiali,Chen Xiaozhen,Wang Chun.Significance of N-Stereogenic Centre in Quaternary Ammonium Salts in Asymmetric Alkylation[J].Chinese Journal of Organic Chemistry,2011,31(3). |
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| Authors: | Lu Jun Liao Xiali Chen Xiaozhen Wang Chun |
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| Institution: | Lu,Juna,b Liao,Xialia,b Chen,Xiaozhena Wang,Chun,a(a Chengdu Institute of Biology,Chinese Academy of Sciences,Chengdu 610041)(b Graduate School of Chinese Academy of Sciences,Beijing 100049) |
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| Abstract: | To elucidate the asymmetric inductive effect of the N-stereogenic centre in quaternary ammo-nium 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 between the ee values of products and the structur... |
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| Keywords: | N-stereogenic quaternary ammonium salt asymmetric catalysis amino acid alkylation |
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