环状酰亚胺不对称还原烷基化的一些结果  

Some Observations on the Asymmetric Reductive Alkylation of Cych'c Imides

作　　者：黄培强[1] 蓝洪桥 陈明德[1] 张洪奎[1] 

机构地区：[1]厦门大学化学系,厦门361005

出　　处：《有机化学》2000年第5期790-794,共5页Chinese Journal of Organic Chemistry

基　　金：国家杰出青年基金(29625204);国家自然科学基金(29832020);高等学校骨干教师资助计划;厦门大学资助

摘　　要：苹果酰亚胺的不对称还原烷基化是合成γ-内酰胺的有效方法,为扩大该法的应用范围,本文研究了多种环状酰亚胺的还原烷基化反应。探讨了影响还原烷基化反应的因素并提出相关的解释。总结出3-取代和3,4-二取代琥珀酰亚胺可成功地进行还原烷基化的规律,并提出了相应的解释。Asymmetric reductive alkylation of malimides is an effective method for the synthesis of optically active N - substituted 5 - alkyl - 4 - benzyloxy - 2 - pyrrolidinones. In order to expand the scope of this method, a study on the reductive alkylation of cyclic imides has been undertaken. Factors affecting the reductive alkylation are discussed and some possible mechanisms are proposed to account for the results obtained. The present study reveals that 3 - substituted and 3,4- disubstituted succinimides are imides suitable for asymmetric reductive alkylation, while the reaction with 3,4 - unsubstituted succinimides led to very low yields. This notable substituent effect is tentatively attributed to the Thorpe - Ingold effect and /or reactive - rotamer effect proposed by Jung.

关 键 词：还原烷基化 2-吡咯烷酮 不对称合成 环状酰亚胺 

分 类 号：O621.25[理学—有机化学]