新型手性螺环季铵盐的合成及其在不对称烷基化中的应用

doi:10.5246/jcps.2011.01.003

新型手性螺环季铵盐的合成及其在不对称烷基化中的应用

王娜, 林松文, 杨青, 孙崎^*, 李润涛^*

北京大学医学部天然药物及仿生药物国家实验室; 药学院化学生物学系, 北京 100191

收稿日期:2010-10-25 修回日期:2010-11-20 出版日期:2011-01-15 发布日期:2011-01-15
通讯作者: 孙崎*, 李润涛*

Synthesis of chiral spirocyclo-quaternary ammonium salts from L-proline and their application as phase-transfer catalysts in asymmetric alkylation

Na Wang, Song-Wen Lin, Qing Yang, Qi Sun^*, Run-Tao Li^*

State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center Beijing 100191, China

Received:2010-10-25 Revised:2010-11-20 Online:2011-01-15 Published:2011-01-15
Contact: Qi Sun*, Run-Tao Li*

摘要/Abstract

摘要：

以L-脯氨酸为起始物设计了一类新型手性相转移催化剂, 并基于对映选择性催化的结果对催化剂的结构进行优化, 最终合成了8个新型手性螺环季铵盐类相转移催化剂, 用于催化N-二苯亚甲基甘氨酸叔丁酯的不对称烷基化反应, 高产率得到烷基化产物, ee 值最高达21%。

关键词: L-脯氨酸, 手性螺环季铵盐, 相转移催化, 不对称烷基化

Abstract:

A new series of chiral phase-transfer catalysts 7a-7h were designed and synthesized from L-proline with moderate to good yields. The catalytic activity of 7a-7h for the asymmetric alkylation of glycine Schiff bases was evaluated, and some interesting relationships between structure and catalytic activity were revealed.

Key words: L-Proline, Quaternary ammonium salts, Phase-transfer catalysts, Asymmetric alkylation

中图分类号:

R916

Supporting:

Foundation items: National Natural Science Foundation of China (Grant No. 20802004).

^*Corresponding author. Tel.: 86-010-82801504;

E-mail: sunqi@bjmu.edu.cn (Qi Sun); lirt@bjmu.edu.cn (Run-Tao Li)

王娜, 林松文, 杨青, 孙崎^*, 李润涛^*. 新型手性螺环季铵盐的合成及其在不对称烷基化中的应用[J]. , DOI: 10.5246/jcps.2011.01.003.

Na Wang, Song-Wen Lin, Qing Yang, Qi Sun^*, Run-Tao Li^*. Synthesis of chiral spirocyclo-quaternary ammonium salts from L-proline and their application as phase-transfer catalysts in asymmetric alkylation [J]. , DOI: 10.5246/jcps.2011.01.003.

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