Concerted Catalysis by Nanocellulose and Proline in Organocatalytic Michael Additions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Effects of Cellulose Nanofibers on Proline-Catalyzed Michael Additions
2.2. Optimization of Reaction Conditions
2.3. Substrate Scope
3. Materials and Methods
3.1. General
3.2. Preparation of TOCNs with Low Carboxylate Content
3.3. Water Removal Process from Nanocellulose Samples
3.4. Representative Procedure for the Proline-Catalyzed Michael Addition of Cyclohexanone to trans-β-Nitrostyrene in the Presence of TOCNs
Spectroscopic Data
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: All data generated and/or compound samples analyzed during this study are included in this article and are available from the corresponding author on reasonable request. |
Entry | Additive | Yield (%) b | syn:antic | ee for syn (%) c |
---|---|---|---|---|
1 | None | 35 | 89:11 | 32 |
2 d | TOCN | 78 | 90:10 | 35 |
3 | TOCN | 88 | 90:10 | 43 |
4 e | TOCN | Trace | - | - |
5 f | TOCN | 81 | 95:5 | 33 |
6 g | TOCN | 86 | 93:7 | -39 |
7 | Sodium acetate | 41 | 89:11 | 6 |
8 h | Carboxymethylcellulose | 34 | 90:10 | 27 |
9 i | TOCN/low carboxylate | 42 | 82:18 | 42 |
Entry | Conditions | TOCN | Yield (%) b | syn:antic | ee for syn (%) c |
---|---|---|---|---|---|
1 | 5 mol% catalyst, rt | − | 37 | 87:13 | 29 |
+ | 74 | 93:7 | 39 | ||
2 | 15 mol% catalyst, rt | − | 58 | 69:31 | 26 |
+ | 77 | 69:31 | 39 | ||
3 | 7.5 mol% catalyst, 0 °C | − | 9 | 77:23 | 19 |
+ | 23 | 74:26 | 39 | ||
4 d | 7.5 mol% catalyst, 40 °C | − | 66 | 94:6 | 32 |
+ | 91 | 94:6 | 42 | ||
5 | Substrate/TOCN (mg/mg) 74.6/25 | + | 51 | 92:8 | 41 |
6 | Substrate/TOCN (mg/mg) 74.6/50 | + | 66 | 94:6 | 43 |
7 | Substrate/TOCN (mg/mg) 74.6/100 | + | 88 | 90:10 | 41 |
8 | Substrate/TOCN (mg/mg) 74.6/150 | + | 63 | 71:29 | 41 |
9 | Substrate/TOCN (mg/mg) 74.6/200 | + | 43 | 83:17 | 43 |
Entry | Substrates | Product | Time (h) | TOCN | Yield (%) b | syn:anti | ee for syn (%) c |
---|---|---|---|---|---|---|---|
1 | | | 48 | − | 26 | 90:10 d | 31 |
48 | + | 68 | 93:7 d | 35 | |||
2 | | | 24 | − | 59 | 96:4 c | 28 |
24 | + | 83 | 95:5 c | 50 | |||
3 | | | 48 | − | 75 | 87:13 d | 10 |
48 | + | 71 | 87:13 d | 21 | |||
4 | | | 24 | − | 18 | 94:6 d | 24 |
24 | + | 76 | 97:3 d | 38 | |||
5 | | | 24 | − | 43 | 61:39 c | 29 |
24 | + | 12 | 72:28 c | 59 | |||
6 | | | 24 | − | 32 | - | 10 |
24 | + | 70 | - | 23 |
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Ranaivoarimanana, N.J.; Kanomata, K.; Kitaoka, T. Concerted Catalysis by Nanocellulose and Proline in Organocatalytic Michael Additions. Molecules 2019, 24, 1231. https://doi.org/10.3390/molecules24071231
Ranaivoarimanana NJ, Kanomata K, Kitaoka T. Concerted Catalysis by Nanocellulose and Proline in Organocatalytic Michael Additions. Molecules. 2019; 24(7):1231. https://doi.org/10.3390/molecules24071231
Chicago/Turabian StyleRanaivoarimanana, Naliharifetra Jessica, Kyohei Kanomata, and Takuya Kitaoka. 2019. "Concerted Catalysis by Nanocellulose and Proline in Organocatalytic Michael Additions" Molecules 24, no. 7: 1231. https://doi.org/10.3390/molecules24071231