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摘要多手性中心的有机分子合成在学术和工业应用等方面都十分重要。特别是催化不对称多组分“多米诺”反应，可以避免耗时，耗财的中间体纯化，以及功能团的保护和去保护等步骤。反应产物环保和具有高度的立体选择性。L-脯氨酸是最早发现的不对称有机小分子催化剂，其结构简单，天然含量非常丰富，价格低廉。随着对脯氨酸的催化性能的深入了解和认识，人们意识到脯氨酸在一些方面还存在很大的局限性。如脯氨酸催化的反应类型及其底物适用范围是有限的， 溶剂的选择也受到一定的限制，基于此，本论文主要研究Jørgenson催化剂催化下，含吲哚酮结构的不饱和双键类化合物与脂肪醛反应，得到所需的手性四氢吡喃衍生物。从催化剂筛选、溶剂、温度等多方面条件优化出反应的最佳条件。并在此基础上扩展了底物，得到了优异的产率、非对映选择性和高效的对映选择性。48167
毕业论文关键词：多米诺反应；有机小分子催化剂; 不对称合成
Abstract
The synthesis of complex organic molecules with multiple chiral centers is important in both academic and industrial laboratories. Especially， the catalytic asymmetric domino reactions of multi component reagents， can avoid the time-consuming， costly intermediate purification， as well as the steps of protection and deprotection functional groups. The reaction process is friendly to environment and with high stereoselectivity. L-proline as the earliest developed asymmetric organocatalysts， the structure is simple and is very rich in nature with low price With the understanding of the catalytic properties of proline， people realize that there are many limitations in some aspects. Such as the limitation of reaction types and substrate scope， the choice of solvent is also subject to certain restrictions. Based on this， our thesis is mainly focused on Jørgenson catalyst asymmetric domino reaction of aldehydes and indole derivatives，affording the required chiral tetrahydropyran derivatives. With the screening of the reaction solvents， temperature etc.， we finally obtained the optimize reaction condition.With the optimized reaction condition in hand， the desired products were obtained in good yields and excellent stereoselectivities.
Keywords， domino reaction； organocatalysis； asymmetric synthesis
目 录
摘要 2
Abstract 3
目录 4
第一章 文献综述 5
1.1 引言 5
1.2 多米诺反应 5
1.3 有机小分子催化发展历史 5
1.4 不对称有机小分子催化剂简介 6
1.4.1 L--脯氨酸催化剂 6
1.4.2 Jørgenson催化剂及其催化的多米诺反应 7
1.5 小结 8
第二章 实验部分 10
2.1 实验仪器 10
2.2 实验试剂 10
3. 底物的制备 11
4. 实验探究 15
5. 数据分析 16
6. 文章总结