Asymmetric Aldol Reactions of α,β-Unsaturated Ketoester Substrates Catalyzed by Chiral Diamines
Abstract
:1. Introduction
2. Result and Discussion
3. Experimental
3.1. General
3.2. General Synthetic Pordecure for Aldol Reactions between α,β-unsaturated Ketoesters and Ketones
4. Conclusions
References and Notes
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- CCDC 802087 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: [email protected]).
Sample Availability: Samples of the compounds 4a-4j are available from the authors. |
Entry | Cat. | Additive | Time | Yield b | Ee c |
---|---|---|---|---|---|
1 | 1a | - | 48 | 62 | 35 |
2 | 1b | TFA | 36 | 98 | 75 |
3 | 1c | TFA | 12 | 97 | 74 |
4 | 1d | TFA | 12 | 94 | 54 |
5 | 1e | TFA | 20 | 88 | 30 |
6 | 1f | TFA | 25 | 96 | 56 |
7 | 1c | HAc | 12 | 97 | 25 |
8 | 1c | PhCO2H | 12 | 97 | 19 |
9 | 1c | TsOH | 42 | 50 | 79 |
10 | 1c | TfOH | 21 | 57 | 82 |
11 d | 1c | TFA | 12 | 97 | 78 |
12 e | 1c | TFA | 12 | 95 | 83 |
13 f | S,S-1c | TFA | 18 | 86 | 71 |
14 g | 1c | TFA | 10 | 87 | 78 |
15 h | 1c | TFA | 10 | 95 | 79 |
Entry | Solvent | Time | Yield | Ee |
---|---|---|---|---|
1 | CH2Cl2 | 19 | 86 | 65 |
2 | Toluene | 19 | 85 | 67 |
3 | THF | 23 | 93 | 59 |
4 | CH3CN | 19 | 90 | 59 |
5 | DMSO | 19 | 95 | 74 |
6 | Et2O | 18 | 96 | 52 |
7 | DMF | 18 | 96 | 68 |
8 | CHCl3 | 18 | 93 | 27 |
9 | CH3CH2OH | 18 | 89 | 53 |
10 | acetone | 12 | 95 | 83 |
11b | acetone | 21 | 97 | 85 |
12c | acetone | 18 | 95 | 91 |
13d | acetone | 120 | 83 | 91 |
Entry | Product | R1 | Yield b | Ee c |
---|---|---|---|---|
1 | 4a | H | 95 | 91 |
2 | 4b | p-CH3 | 96 | 90 |
3 | 4c | p-NO2 | 91 | 96 |
4 | 4d | p-OMe | 95 | 93 |
5 | 4e | p-F | 93 | 92 |
6 | 4f | p-Br | 96 | 94 |
7 | 4g | p-Cl | 91 | 92 |
8 | 4h | p-CN | 96 | 95 |
9 | 4i | m-CH3 | 86 | 92 |
10 | 4j | m-OMe | 91 | 92 |
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Kan, S.-S.; Li, J.-Z.; Ni, C.-Y.; Liu, Q.-Z.; Kang, T.-R. Asymmetric Aldol Reactions of α,β-Unsaturated Ketoester Substrates Catalyzed by Chiral Diamines. Molecules 2011, 16, 3778-3786. https://doi.org/10.3390/molecules16053778
Kan S-S, Li J-Z, Ni C-Y, Liu Q-Z, Kang T-R. Asymmetric Aldol Reactions of α,β-Unsaturated Ketoester Substrates Catalyzed by Chiral Diamines. Molecules. 2011; 16(5):3778-3786. https://doi.org/10.3390/molecules16053778
Chicago/Turabian StyleKan, Sha-Sha, Jian-Zhen Li, Cheng-Yan Ni, Quan-Zhong Liu, and Tai-Ran Kang. 2011. "Asymmetric Aldol Reactions of α,β-Unsaturated Ketoester Substrates Catalyzed by Chiral Diamines" Molecules 16, no. 5: 3778-3786. https://doi.org/10.3390/molecules16053778