Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst
Abstract
:1. Introduction
2. Results and Discussion
Entry | Cat. | Solvent | Time (h) | Yield (%) a | ee (%) b |
---|---|---|---|---|---|
1 | I | PhMe | 3 | 73 | 5 |
2 | II | PhMe | 3 | 76 | 5 |
3 | III | PhMe | 2 | 82 | 25 |
4 | IV | PhMe | 5 | 83 | 15 |
5 | V | PhMe | 2 | 88 | 91 |
6 | VI | PhMe | 2 | 80 | 67 |
7 | III | CH2Cl2 | 2 | 90 | 83 |
8 | III | THF | 3 | 78 | 81 |
9 | III | Et2O | 3 | 86 | 73 |
10 | III | p-xylene | 4 | 78 | 87 |
11 | III | m-xylene | 4 | 81 | 85 |
12 c | V | PhMe | 5 | 83 | 87 |
13 d | V | PhMe | 5 | 70 | 59 |
Entry | 1, Ar | Yield (%) a | ee (%) b |
---|---|---|---|
1 | 1a, Ph | 88 | 3a, 91 |
2c | 1b, m-MeC6H4 | 91 | 3b, 83 |
3 | 1c, p-MeC6H4 | 88 | 3c, 81 |
4 | 1d, m-MeOC6H4 | 86 | 3d, 91 |
5 c | 1e, p-FC6H4 | 87 | 3e, 85 |
6 | 1f, 2-naphthyl | 82 | 3f, 83 |
3. Experimental
3.1. General
3.2. Typical Procedure for the Conjugate Addition Reaction of 3-Phenyloxindole (1a) with Methyl Vinyl Ketone (2a)
3.3. Typical Procedure for the Conjugate Addition Reaction of 3-Phenyloxindole (1a) with 1,1-Bis(benzenesulfonyl)ethylene (4a)
4. Conclusions
Acknowledgments
- Sample Availability: Samples of the compounds 3 and 5 are available from the authors.
References and Notes
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Lee, H.J.; Woo, S.B.; Kim, D.Y. Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst. Molecules 2012, 17, 7523-7532. https://doi.org/10.3390/molecules17067523
Lee HJ, Woo SB, Kim DY. Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst. Molecules. 2012; 17(6):7523-7532. https://doi.org/10.3390/molecules17067523
Chicago/Turabian StyleLee, Hyun Joo, Saet Byeol Woo, and Dae Young Kim. 2012. "Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst" Molecules 17, no. 6: 7523-7532. https://doi.org/10.3390/molecules17067523