大学化学2024，Vol.39Issue(5)：154-162,9.DOI:10.3866/PKU.DXHX202310074
脯氨酸催化的不对称羟醛缩合反应的改进与拓展
Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction
鲁鸿 1翟奕蝶 1成星星 1高钰佳 1魏青 1魏颢1
作者信息
- 1. 西北大学化学与材料科学学院,化学国家级实验教学示范中心,西安 710127
- 折叠
摘要
Abstract
The proline-catalyzed asymmetric aldol reaction stands as a classic experiment illustrating the concept of enantiomerism.However,due to substrate reactivity limitations and experimental constraints,the stereochemical concepts of diastereoisomerism and racemization have not been adequately addressed.To bridge this gap between experimental and theoretical teaching and enhance students'understanding of stereochemistry in Organic Chemistry,we have innovated and expanded the proline-catalyzed asymmetric aldol reaction.Firstly,by upgrading the conventional two-component reaction to a three-component reaction,we efficiently generate diastereomers through the conversion of arylaldehydes to highly reactive aldimines.Secondly,we introduce the stereoselective control of proline through the use of catalysts with opposite chiral configurations,while also incorporating the concept of racemization by mixing products with opposite configurations.Thirdly,we employ nuclear magnetic resonance(NMR)technology to elucidate the diastereoisomerism ratio of the products,facilitating a deeper understanding of diastereoisomerism concepts.Our results demonstrate that this experiment offers excellent repeatability,appropriate duration,and a balance of exploration and innovation.Implementation of this project not only enhances students'scientific inquiry and innovative thinking but also cultivates their ability to conduct innovative experiments.关键词
不对称催化/立体化学/立体选择性/核磁共振谱图Key words
Asymmetric catalysis/Stereochemistry/Stereoselectivity/NMR spectroscopy分类
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鲁鸿,翟奕蝶,成星星,高钰佳,魏青,魏颢..脯氨酸催化的不对称羟醛缩合反应的改进与拓展[J].大学化学,2024,39(5):154-162,9.
