新型C3-含硅基取代手性脯氨酸型催化剂的高效构筑

doi:10.16183/j.cnki.jsjtu.2021.038

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

中图分类号:

O621.3

谭富欣, 李子昊, 周佳, 张书宇. 新型C3-含硅基取代手性脯氨酸型催化剂的高效构筑[J]. 上海交通大学学报, 2021, 55(9): 1058-1063.

TAN Fuxin, LI Zihao, ZHOU Jia, ZHANG Shuyu. Efficient Construction of Novel C3-Silyl Substituted Chiral Proline Catalysts[J]. Journal of Shanghai Jiao Tong University, 2021, 55(9): 1058-1063.

图/表 5

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