Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Procedure for the Synthesis of Benzimidazole-Based Organocatalysts 1–10
3.2. General Procedure for the Asymmetric Amination of 1,3-Dicarbonyl Compounds
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References and Notes
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Sample Availability: Not available. |
Entry | Catalyst | Conv. (%) b | ee (%) c |
---|---|---|---|
1 | 1 | 95 | 91 |
2 | 2 | 90 | 66 |
3 | 3 | 93 | 90 |
4 | 4 | 96 | 78 |
5 | 5 | 65 | 40 |
6 | 6 | 57 | 33 |
7 | 7 | 22 | Rac |
8 | 8 | 85 | 76 |
9 | 9 | 40 | 10 |
10 | 10 | ~15 | 27 |
Entry | Catalyst (x mol %) | Solvent | Temp. (°C) | Conv. (%) b | ee (%) c |
---|---|---|---|---|---|
1 | 1 (10 mol %) | toluene | 25 | 95 | 91 |
2 | 1 (10 mol %) | hexane | 25 | 97 | 85 |
3 | 1 (10 mol %) | Et2O | 25 | 99 | 70 |
4 | 1 (10 mol %) | CH2Cl2 | 25 | 99 | 74 |
5 | 1 (10 mol %) | toluene | 0 | 87 | 92 |
6 | 1 (5 mol %) | toluene | 25 | 95 | 84 |
7 | 3 (5 mol %) | toluene | 25 | 90 | 85 |
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Benavent, L.; Puccetti, F.; Baeza, A.; Gómez-Martínez, M. Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds. Molecules 2017, 22, 1333. https://doi.org/10.3390/molecules22081333
Benavent L, Puccetti F, Baeza A, Gómez-Martínez M. Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds. Molecules. 2017; 22(8):1333. https://doi.org/10.3390/molecules22081333
Chicago/Turabian StyleBenavent, Llorenç, Francesco Puccetti, Alejandro Baeza, and Melania Gómez-Martínez. 2017. "Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds" Molecules 22, no. 8: 1333. https://doi.org/10.3390/molecules22081333