Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Diprolinamide Organocatalyst
2.2. Evaluation of Ionic Solution Effects
3. Conclusion
Supplementary Material
ijms-12-09083-s001.pdfAcknowledgements
References and Notes
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Entry | Cation | Anion | Yield (%) a | dr (%) a anti/syn | ee (%) b |
---|---|---|---|---|---|
1 c | - | - | 91 | >99/1 | >99 |
2 d | - | - | 7 | 81/19 | 22 |
3 | Na | F | 49 | 83/17 | 67 |
4 | Na | Cl | 54 | 82/18 | 87 |
5 | Na | Br | 30 | 78/22 | 43 |
6 | Na | I | 17 | 79/21 | 34 |
7 | Na | OAc | 75 | 81/19 | 38 |
8 | K | F | 23 | 79/22 | 67 |
9 | K | Cl | 27 | 83/17 | 45 |
10 | K | Br | 44 | 80/20 | 35 |
11 | K | I | 32 | 75/25 | 21 |
12 | Mg | Cl2 | 55 | 80/20 | 51 |
13 | Ca | Cl2 | 99 | 45/55 | 2 |
Entry | Cation | Anion | Yield (%) a | de (%) b anti/syn | ee (%) c |
---|---|---|---|---|---|
1 | Cu | Cl | trace d | - | - |
2 | Cu | Br2 | trace d | - | - |
3 | Fe(III) | Cl3 | >99 | 42/58 | 0 |
4 | Ni | Cl2 | 3 | 82/18 | 83 |
5 | Zn | OAc | >99 | 80/20 | 92 |
Entry | EDTA (% w/w) | Yield (%) a | de (%) a | ee (%) b |
---|---|---|---|---|
1 | 0 | 7 | 81 | 22 |
2 c | 5 | 0 | - | - |
3 | 5 | 98 | 84 | 51 |
Entry | Aldehyde | n | Salt | Conversion a | dr a (anti/syn) | ee b |
---|---|---|---|---|---|---|
1 | 8a | 1 | N/A c | 45 | 92/8 | 68 |
2 | 8a | 1 | N/A d | 82 | 84/16 | 28 |
3 | 8a | 1 | EDTA e | 98 | 83/17 | 25 |
4 | 8a | 1 | Zn(OAc)2 | 44 | 76/24 | 4 |
5 | 8b | 1 | N/A c | 21 | 91/9 | 92 |
6 | 8b | 1 | N/A d | 80 | 86/14 | 68 |
7 | 8b | 1 | EDTA e | 70 | 85/15 | 88 |
8 | 8b | 1 | Zn(OAc)2 | 70 | 76/24 | 64 |
9 | 6 | 0 | N/A c | 61 | 76/24 | 14 |
10 | 6 | 0 | N/A d | 56 | 39/61 | 22 |
11 | 6 | 0 | EDTA e | 74 | 34/66 | 13 |
12 | 6 | 0 | Zn(OAc)2 | 97 | 29/71 | 14 |
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Delaney, J.P.; Henderson, L.C. Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions. Int. J. Mol. Sci. 2011, 12, 9083-9094. https://doi.org/10.3390/ijms12129083
Delaney JP, Henderson LC. Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions. International Journal of Molecular Sciences. 2011; 12(12):9083-9094. https://doi.org/10.3390/ijms12129083
Chicago/Turabian StyleDelaney, Joshua P., and Luke C. Henderson. 2011. "Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions" International Journal of Molecular Sciences 12, no. 12: 9083-9094. https://doi.org/10.3390/ijms12129083