谭富欣, 李子昊, 周佳, 张书宇()

上海市手性药物分子工程重点实验室, 上海 200240

收稿日期:2021-02-05出版日期:2021-09-28发布日期:2021-10-08
通讯作者:张书宇E-mail:zhangsy16@sjtu.edu.cn
作者简介:谭富欣(1995-),男,河南省南阳市人,硕士生,主要从事有机合成方法学的研究
基金资助:国家自然科学基金资助项目(22071147)

Efficient Construction of Novel C3-Silyl Substituted Chiral Proline Catalysts

TAN Fuxin, LI Zihao, ZHOU Jia, ZHANG Shuyu()

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai 200240, China

Received:2021-02-05Online:2021-09-28Published:2021-10-08
Contact:ZHANG Shuyu E-mail:zhangsy16@sjtu.edu.cn

摘要/Abstract

摘要： 为将C-H活化策略应用于手性有机催化剂的开发,选择以L-脯氨酸为原料、C(sp³)-H硅烷化反应为关键步骤,设计合成了两种新型的C3-三甲基硅基取代的手性脯氨酸催化剂,并将其分别应用于对硝基苯甲醛与丙酮的分子间不对称aldol反应和亚胺与β-甲基丁醛的分子间不对称Mannich反应,均可以良好对映选择性实现目标产物的合成.该策略有效丰富了脯氨酸结构的修饰手段,为新型含硅小分子催化剂的开发提供了新方法.
关键词: C(sp³)-H硅烷化, 脯氨酸, 有机催化
Abstract: In order to apply the C-H activation strategy to the development of chiral organic catalysts, two novel C3-trimethylsilyl substituted chiral proline catalysts are designed and synthesized using L-proline as the starting material and C(sp ³)-H silylation as the key step, which are applied to the asymmetric aldol reaction of p-nitrobenzaldehyde with acetone and the asymmetric Mannich reaction of imine with β-methylbutyraldehyde, respectively. Both target products can be synthesized with a good enantioselectivity. This strategy effectively enriches the means of structural modification of proline and provids a new method for the development of new silicon-containing organic catalysts.
Key words: C(sp³)-H silylation, proline, organic catalysis


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