Application Scope and Limitations of TADDOL-Derived Chiral Ammonium Salt Phase-Transfer Catalysts
Abstract
:1. Introduction
2. Results and Discussion
2.1. Late Stage Catalyst Modification
2.2. Asymmetric α-Alkylation of β-Keto Esters
2.3. Asymmetric Michael Addition Reactions of Glycine Schiff Bases
Entry a | Cat. (mol%) | 4 | 12 | Solv. | Base (eq.) | T [°C] | 13 | Yield b [%] | e.r. c (conf.) d |
---|---|---|---|---|---|---|---|---|---|
1 | 3a (10%) | 4a | 12a | toluene | KOH (50%) (25×) | 0 | 13a | 94 | 51:49 (S) |
2 | 3a (10%) | 4a | 12a | toluene | KOH (50%) (1×) | 0 | 13a | 88 | 50:50 |
3 | 3a (10%) | 4a | 12a | toluene | KOH (s) (20×) | 0 | 13a | 76 | 50:50 |
4 | 3a (10%) | 4a | 12a | toluene | K3PO4 (50%) (10×) | 0 | 13a | 34 | 50:50 |
5 | 3a (10%) | 4a | 12a | toluene | K2CO3 (50%) (10×) | 0 | 13a | 18 | 52:48 (S) |
6 | 3a (10%) | 4a | 12a | toluene | Cs2CO3 (70%) (10×) | 0 | 13a | 10 | 50:50 |
7 | 3a (10%) | 4a | 12a | toluene | Cs2CO3 (s) (20×) | 0 | 13a | 73 | 66:34 (S) |
8 | 3a (10%) | 4a | 12a | toluene | Cs2CO3 (s) (20×) | −20 | 13a | 56 | 71:29 (S) |
9 e | 3a (10%) e | 4a | 12a | toluene | Cs2CO3 (s) (20×) | −20 | 13a | 62 | 61:39 (S) |
10 | 3d (10%) | 4a | 12a | toluene | Cs2CO3 (s) (20×) | −20 | 13a | 14 | 62:38 (S) |
11 | 3e (10%) | 4a | 12a | toluene | Cs2CO3 (s) (20×) | −20 | 13a | 82 | 64:36 (S) |
12 | 3a (10%) | 4a | 12a | benzene | Cs2CO3 (s) (20×) | 0 | 13a | 72 | 58:42 (S) |
13 | 3a (10%) | 4a | 12a | fluorobenzene | Cs2CO3 (s) (20×) | 0 | 13a | 89 | 54:46 (S) |
14 | 3a (10%) | 4a | 12a | mesitylene | Cs2CO3 (s) (20×) | 0 | 13a | 74 | 69:31 (S) |
15 f | 3a (10%) | 4a | 12a | mesitylene | Cs2CO3 (s) (20×) | 0 | 13a | 33 | 57:43 (S) |
16 g | 3a (10%) | 4a | 12a | mesitylene | Cs2CO3 (s) (20×) | 0 | 13a | 76 | 51:49 (S) |
17 | 3a (10%) | 4b | 12a | mesitylene | Cs2CO3 (s) (20×) | 0 | 13b | 66 | 75:25 (S) |
18 | 3a (10%) | 4c | 12a | mesitylene | Cs2CO3 (s) (20×) | 0 | 13c | 81 | 78:22 |
19 | 3a (10%) | 4c | 12a | mesitylene | Cs2CO3 (s) (20×) | −20 | 13c | 35 | 85:15 |
20 | 3a (20%) | 4c | 12a | mesitylene | Cs2CO3 (s) (20×) | −20 | 13c | 71 | 90:10 |
21 | 3a (20%) | 4c | 12b | mesitylene | Cs2CO3 (s) (20×) | −20 | 13d | 68 | 89:11 |
22 | 3a (20%) | 4c | 12c | mesitylene | Cs2CO3 (s) (20×) | −20 | 13e | n.r. | n.d. |
23 | 3a (20%) | 4c | 12d | mesitylene | Cs2CO3 (s) (20×) | −20 | 13f | 81 | 87:13 |
24 | 3f (20%) | 4c | 12a | mesitylene | Cs2CO3 (s) (20×) | −20 | 13c | 51 | 80:20 |
25 | 3g (20%) | 4c | 12a | mesitylene | Cs2CO3 (s) (20×) | −20 | 13c | 56 | 86:14 |
26 | 3h (20%) | 4c | 12a | mesitylene | Cs2CO3 (s) (20×) | −20 | 13c | 68 | 91:9 |
Entry | 4 | Acceptor (eq.) | Solv. | Base (eq.) | T [°C] | t [h] | Prod. | Yield a [%] | e.r. b |
---|---|---|---|---|---|---|---|---|---|
1 | 4a | 14a (2×) | mesitylene | Cs2CO3 (s) (20×) | 0 | 20 | 16a | 32 | 50:50 |
2 | 4a | 14a (2×) | mesitylene | Cs2CO3 (s) (1×) | 0 | 20 | 16a | 11 | 50:50 |
3 | 4a | 14a (2×) | toluene | K2CO3 (s) (1×) | 0 | 20 | 16a | n.r. | n.d. |
4 | 4a | 14a (2×) | toluene | K2HPO4 (s) (1×) | 0 | 20 | 16a | n.r. | n.d. |
5 | 4a | 14a (2×) | toluene | KOH (s) (1×) | 0 | 20 | 16a | 55 | 56:44 |
6 | 4a | 14a (2×) | toluene | KOH (50%) (25×) | 0 | 20 | 16a | 62 | 65:35 |
7 | 4a | 14a (2×) | toluene | CsOH (50%) (25×) | 0 | 20 | 16a | 55 | 66:34 |
8 | 4a | 14a (2×) | toluene | RbOH (50%) (25×) | 0 | 20 | 16a | 69 | 69:31 |
9 | 4a | 14a (2×) | mesitylene | RbOH (50%) (25×) | 0 | 20 | 16a | 62 | 60:40 |
10 | 4a | 14a (2×) | toluene | RbOH (50%) (25×) | −20 | 48 | 16a | 65 | 75:25 |
11 | 4a | 14b (2×) | toluene | RbOH (50%) (25×) | −20 | 48 | 16b | 81 | 60:40 |
12 | 4c | 14b (2×) | toluene | RbOH (50%) (25×) | −20 | 48 | 16c | 64 | 57:43 |
13 | 4c | 15 (2×) | toluene | RbOH (50%) (25×) | −20 | 48 | 17 | 65 | 67:33 (S) c |
14 | 4c | 15 (1.5×) | mesitylene | Cs2CO3 (s) (20×) | −20 | 48 | 17 | 97 | 77:23 (S) c |
3. Experimental
3.1. General
3.2. Conditions A: General Procedure for the Phase-Transfer Catalysed Michael-Reaction under Liquid/Solid Phase-Transfer Conditions
3.3. Conditions B: General Procedure for the Phase-Transfer Catalysed Michael-Reaction under Liquid/Liquid Phase-Transfer Conditions
4. Conclusions
Supplementary Materials
Acknowledgments
References
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Gururaja, G.N.; Herchl, R.; Pichler, A.; Gratzer, K.; Waser, M. Application Scope and Limitations of TADDOL-Derived Chiral Ammonium Salt Phase-Transfer Catalysts. Molecules 2013, 18, 4357-4372. https://doi.org/10.3390/molecules18044357
Gururaja GN, Herchl R, Pichler A, Gratzer K, Waser M. Application Scope and Limitations of TADDOL-Derived Chiral Ammonium Salt Phase-Transfer Catalysts. Molecules. 2013; 18(4):4357-4372. https://doi.org/10.3390/molecules18044357
Chicago/Turabian StyleGururaja, Guddeangadi N., Richard Herchl, Antonia Pichler, Katharina Gratzer, and Mario Waser. 2013. "Application Scope and Limitations of TADDOL-Derived Chiral Ammonium Salt Phase-Transfer Catalysts" Molecules 18, no. 4: 4357-4372. https://doi.org/10.3390/molecules18044357