Diastereoselective Synthesis of Cyclopentanediols by InCl3/Al Mediated Intramolecular Pinacol Coupling Reaction in Aqueous Media
Abstract
:Introduction
Results and Discussion
Screening of reaction temperature
Investigation of the scope of the InCl3/Al catalyzed intramolecular pinacol coupling
Entry | Diketone | Product | Yield (%)b | d. e. (%)c | |
---|---|---|---|---|---|
R1 | R2 | ||||
1 | H | H | 2a | 65 | > 99 |
2 | H | 4-CH3 | 2b | 78 | > 99 |
3 | H | 4-CH3O | 2c | 75 | 58 |
4 | H | 4-Cl | 2d | 62 | > 99 |
5 | 4-CH3 | H | 2e | 80 | > 99 |
6 | 4-Cl | H | 2f | 83 | > 99 |
7 | 4-CH3O | H | 2g | 88 | > 99 |
8 | 2-Cl | H | 2h | 61 | 44 |
9 | 4-CH3 | 4-CH3 | 2i | 90 | > 99 |
10 | 4-F | H | 2j | 79 | > 99 |
11 | 4-N(CH3)2 | H | - | trace | - |
12 | - | - | - | ||
13d | |||||
14e | nr |
Experimental
General
General procedure of the intramolecular pinacol coupling reaction
Acknowledgements
References
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Chen, Y.; Wan, J.; Wang, C.; Sun, C. Diastereoselective Synthesis of Cyclopentanediols by InCl3/Al Mediated Intramolecular Pinacol Coupling Reaction in Aqueous Media. Molecules 2008, 13, 2652-2658. https://doi.org/10.3390/molecules13102652
Chen Y, Wan J, Wang C, Sun C. Diastereoselective Synthesis of Cyclopentanediols by InCl3/Al Mediated Intramolecular Pinacol Coupling Reaction in Aqueous Media. Molecules. 2008; 13(10):2652-2658. https://doi.org/10.3390/molecules13102652
Chicago/Turabian StyleChen, Yunhua, Jieping Wan, Chunyan Wang, and Cuirong Sun. 2008. "Diastereoselective Synthesis of Cyclopentanediols by InCl3/Al Mediated Intramolecular Pinacol Coupling Reaction in Aqueous Media" Molecules 13, no. 10: 2652-2658. https://doi.org/10.3390/molecules13102652