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Citation: Renxiao Liang, Zhe Zhong, Zhangling Jin, Lijuan Shi, Yixia Jia. A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline[J]. University Chemistry, ;2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024 shu

A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline

1.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China;
2.
School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China

Received Date: 6 November 2023
Revised Date: 5 January 2024

we establish a relay catalysis strategy utilizing Pd(OAc)₂/chiral phosphoric acid catalyst for the efficient synthesis of optically active 2-phenyl tetrahydroquinoline via a one-pot three-step domino reaction of 2-iodoaniline with allylic alcohol, eliminating the need for intermediate isolation. Compared to conventional single catalysis methods, this cooperative relay catalysis offers advantages of simplicity and high efficiency. Introducing scientific frontiers such as cooperative relay catalysis into experimental teaching, along with principles of green chemistry and energy saving, broadens students’ scientific perspectives, ignites their passion for learning, and enhances their innovation capabilities. Furthermore, this experiment encompasses fundamental theoretical knowledge including Grignard reactions, Heck reactions, imine condensations, and asymmetric hydrogen transfers, alongside practical analytical techniques such as thin-layer chromatography (TLC), column chromatography, nuclear magnetic resonance (NMR), rotary evaporation, high-performance liquid chromatography (HPLC), and polarimetry. Through this comprehensive experiment, students’ theoretical understanding, experimental skills, and scientific reasoning abilities are enriched, fostering the integration of scientific research and teaching.
- Relay catalysis,
- Domino reaction,
- Asymmetric synthesis,
- Tetrahydroquinoline
1. [1]
2. [2]
3. [3]
4. [4]
  Tietze, L. F. Chem. Rev. 1996, 96(1), 115.
5. [5]
  D’Souza, D. M.; Müller, T. J. J. Chem. Soc. Rev. 2007, 36(1), 1095.
6. [6]
  Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40(20), 3726.
7. [7]
  Shao, Z.; Zhang, H. Chem. Soc. Rev. 2009, 38(9), 2745.
8. [8]
9. [9]
10. [10]
  Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28(1), 2.
11. [11]
  You, S.-L. Chem. Asian J. 2007, 2(7), 820.
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