季铵盐中N-手性在不对称烷基化反应中的作用研究  

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

作　　者：鲁军[1,2] 廖霞俐[1,2] 陈晓珍[1] 王淳[1] 

机构地区：[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

出　　处：《有机化学》2011年第3期341-345,共5页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20672108)资助项目

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.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 structures of catalysts indicated that the N-stereogenic centre alone showed no significant effect on the enantioselectivity of alkylation.

关 键 词：N-手性季铵盐 不对称催化 氨基酸 烷基化 

分 类 号：O643.32[理学—物理化学]