Application of Polyamines and Amino Acid Derivatives Based on 2-Azabicycloalkane Backbone in Enantioselective Aldol Reaction
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Measurements
3.2. Preparation of Compounds
3.2.1. Synthesis of Starting Compounds
3.2.2. Preparation of Polyamines (5, 6, 11, 10, 13)
3.2.3. General Procedure for Amide Synthesis
3.2.4. Catalytic Reactions
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Entry | Catalyst | Ketone | Solvent | Yield [%] d | anti/syne | ee [%] f |
---|---|---|---|---|---|---|
1 a | l-proline | acetone | neat | >95 | - | 66 (R) |
2 a | 4 | acetone | neat | 89 | - | 22 (R) |
3 a | 8 | acetone | neat | <8 | - | - |
4 a | 9 | acetone | neat | 59 g | - | 60 (R) |
5 a | 12 | acetone | neat | 15 | - | 52 (R) |
6 b | l-proline | cyclohexanone | CHCl3 | 26 | 73:27 | (anti) 63(syn) 56 |
7 b | 4 | cyclohexanone | CHCl3 | 13 | 79:21 | (anti) 11(syn) 6 |
8 b | 6 | cyclohexanone | CHCl3 | 16 | 26:74 | (anti) 22(syn) 0 |
9 b | 8 | cyclohexanone | CHCl3 | traces | - | - |
10 b | 9 | cyclohexanone | CHCl3 | >95 h | 78:22 | (anti) 57(syn) 15 |
11 b | 10 | cyclohexanone | CHCl3 | traces | - | - |
12 b | 11 | cyclohexanone | CHCl3 | 43 | 26:74 | (anti) 20(syn) 21 |
13 b | 12 | cyclohexanone | CHCl3 | 63 e | 84:16 | (anti) 38(syn) 40 |
14 b | 13 | cyclohexanone | CHCl3 | 0 | - | - |
15 c | l-proline | cyclohexanone | brine | traces | - | - |
16 c | 4 | cyclohexanone | brine | traces | - | - |
17 c | 6 | cyclohexanone | brine | 86 | 65:35 | (anti) 16(syn) 31 |
18 c | 8 | cyclohexanone | brine | traces | - | - |
19 c | 9 | cyclohexanone | brine | >95 | 73:27 | (anti) 63(syn) 44 |
20 c | 10 | cyclohexanone | brine | traces | - | - |
21 c | 11 | cyclohexanone | brine | >95 | 81:19 | (anti) 3(syn) 14 |
22 c | 12 | cyclohexanone | brine | traces | - | - |
23 c | 13 | cyclohexanone | brine | traces | - | - |
Sample | Fractions | Mass/mg | dr (anti:syn) | ee (anti)/% | ee (syn)/% |
---|---|---|---|---|---|
1 | Raw mixture | 16.0 | 88:12 | 3 | 11 |
1 | 1.6 | 85:15 | 5 | 11 | |
2 | 5.5 | 95:5 | 2 | 14 | |
3 | 1.7 | 97:3 | 2 | 9 | |
4 | 5.4 | 97:3 | 2 | 12 | |
5 | 1.7 | 97:3 | 2 | 11 | |
2 | Raw mixture | 60.0 | 24:76 | 57 | 15 |
1 | 8.6 | 33:67 | nd b | ||
2 | 27.5 | 19:81 | 61 | 4 | |
3 | 18.6 | 1:99 | 43 | 15 | |
4 | 2.9 | 1:99 | 52 | 46 | |
3 | Raw mixture | 48.0 | 80:20 | 54 | 52 |
1 | 16.9 | 57:43 | nd b | ||
2 | 17.6 | 88:12 | 48 | 6 | |
3 | 13.5 | 98:2 | 61 | 56 |
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Iwan, D.; Kamińska, K.; Wojaczyńska, E. Application of Polyamines and Amino Acid Derivatives Based on 2-Azabicycloalkane Backbone in Enantioselective Aldol Reaction. Molecules 2021, 26, 5166. https://doi.org/10.3390/molecules26175166
Iwan D, Kamińska K, Wojaczyńska E. Application of Polyamines and Amino Acid Derivatives Based on 2-Azabicycloalkane Backbone in Enantioselective Aldol Reaction. Molecules. 2021; 26(17):5166. https://doi.org/10.3390/molecules26175166
Chicago/Turabian StyleIwan, Dominika, Karolina Kamińska, and Elżbieta Wojaczyńska. 2021. "Application of Polyamines and Amino Acid Derivatives Based on 2-Azabicycloalkane Backbone in Enantioselective Aldol Reaction" Molecules 26, no. 17: 5166. https://doi.org/10.3390/molecules26175166