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.