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Citation: Mo Li, Huang Kejun, Yang Zhixiang, Chen Pingping, Chen Zhiming. Reaction of Tetrahydrothiopyran-4-one and Aromatic Aldehyde Catalysized by C₂ Axiallyl Chiral Biaryl Compounds[J]. Chemistry, ;2018, 81(8): 727-733. shu

Reaction of Tetrahydrothiopyran-4-one and Aromatic Aldehyde Catalysized by C₂ Axiallyl Chiral Biaryl Compounds

Key Laboratory of Functional Materials Chemistry of Guizhou Province, School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001

Corresponding author: Chen Zhiming, czm000219@163.com
Received Date: 19 March 2018
Accepted Date: 17 April 2018

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In this paper, four kinds of C₂ axis chiral biaryl organic catalysts were successfully synthesized and used to catalyze the reaction of tetrahydrothiopyran-4-one and aromatic aldehydes. It is demonstrated that using dichloromethane as solvent, the molar ratio of aromatic aldehyde and tetrahydrothiopyran-4-one is 1.2:5, the dosage of catalyst is 10(mol)%, the temperature and time of reaction are 0℃ and 20 h, the target products can be obtained with higher yield (up to 85%) and better stereoselectivity (up to 86%).
- C₂ axially chiral biary,
- Tetrahydrothiopyran-4-one,
- Aromatic aldehyde
1. [1]
  H Matsuyama, Y Miyazawa, Y Takei et al. Chem. Lett., 1984, 20(5):833~836.
2. [2]
  Z Fang, H Yuan, Y Liu et al. Chem. Commun., 2012, 48(70):8802~8804.
3. [3]
  H Nakazumi, T Ueyama, T Kitao. J. Heterocycl. Chem., 1985, 22(6):1593~1596.
4. [4]
  M S Abaee, M M Mojtahedi, G F Pasha et al. Org. Lett., 2011, 13(19):5282~5285.
5. [5]
6. [6]
7. [7]
  A Dondoni, A Massi. Angew. Chem. Int. Ed., 2008, 47:4638~4660.
8. [8]
  B List, R A Lerner, C F Barbas. J. Am. Chem. Soc., 2000, 122(10):2395~2396.
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
  D Enders, P Fey, H Kipphardt. Organic Syntheses. John Wiley & Sons, Inc. 2003:173~173.
14. [14]
  A F Spatola, M K Anwer, A L Rockwell et al. J. Am. Chem. Soc., 1986, 108(4):825~831.
15. [15]
  N Dahlin, A Bøgevig, H Adolfsson. Adv. Synth. Catal., 2004, 346(9-10):1101~1105.
16. [16]
  A F Spatola, M K Anwer, A L Rockwell et al. J. Am. Chem. Soc., 2002, 108(4):825~831.
1. [1]
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2. [2]
  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. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
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Reaction of Tetrahydrothiopyran-4-one and Aromatic Aldehyde Catalysized by C2 Axiallyl Chiral Biaryl Compounds

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通讯作者: 陈斌, bchen63@163.com

Reaction of Tetrahydrothiopyran-4-one and Aromatic Aldehyde Catalysized by C₂ Axiallyl Chiral Biaryl Compounds