Home

Citation: Hong Lu, Yidie Zhai, Xingxing Cheng, Yujia Gao, Qing Wei, Hao Wei. Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction[J]. University Chemistry, ;2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074 shu

Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction

National Demonstration Center for Experiment Chemistry Education, College of Chemistry & Materials Science, Northwest University, Xi’an 710127, China

Received Date: 19 October 2023
Revised Date: 8 January 2024

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.
- Asymmetric catalysis,
- Stereochemistry,
- Stereoselectivity,
- NMR spectroscopy
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
  List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122(10), 2395.
6. [6]
  Córdova, A.; Notz, W.; Barbas, C. F. Chem. Commun. 2002, 3024.
7. [7]
  List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124(5), 827.
8. [8]
  Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F. J. Am. Chem. Soc. 2007, 129(2), 288.
1. [1]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
2. [2]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
3. [3]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037
4. [4]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
5. [5]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
6. [6]
  Yongming Zhu , Huili Hu , Yuanchun Yu , Xudong Li , Peng Gao . Construction and Practice on New Form Stereoscopic Textbook of Electrochemistry for Energy Storage Science and Engineering: Taking Basic Course of Electrochemistry as an Example. University Chemistry, 2024, 39(8): 44-47. doi: 10.3866/PKU.DXHX202312086
7. [7]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
8. [8]
  Chengxia Tong , Yajie Li , Jin Yan , Xuejian Qu , Shigang Wei , Yong Fan , Zhiguang Song , Yupeng Guo . The Construction and Practice of a Comprehensive and Three-Dimensional Practical Education Model. University Chemistry, 2024, 39(7): 49-55. doi: 10.12461/PKU.DXHX202404155
9. [9]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
10. [10]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
11. [11]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
12. [12]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
13. [13]
  Jinkang Jin , Yidian Sheng , Ping Lu , Zhan Lu . Introducing a Website for Learning Nuclear Magnetic Resonance (NMR) Spectrum Analysis. University Chemistry, 2024, 39(11): 388-396. doi: 10.12461/PKU.DXHX202403054
14. [14]
  Haolin Zhan , Qiyuan Fang , Jiawei Liu , Xiaoqi Shi , Xinyu Chen , Yuqing Huang , Zhong Chen . Noise Reduction of Nuclear Magnetic Resonance Spectroscopy Using Lightweight Deep Neural Networ. Acta Physico-Chimica Sinica, 2025, 41(2): 100017-. doi: 10.3866/PKU.WHXB202310045
15. [15]
  Haiyang Jin , Yonghai Hui , Yongfei Zhang , Lijun Gao , Yun Wang . Application and Exploration of Nuclear Magnetic Resonance Spectrometer in Undergraduate Basic Laboratory Teaching. University Chemistry, 2025, 40(3): 245-250. doi: 10.12461/PKU.DXHX202406022
16. [16]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
17. [17]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
18. [18]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
19. [19]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
20. [20]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(259)
HTML views(137)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return