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Direct Enantioselective Michael Addition of Aldehydes to Vinyl Ketones Catalyzed by Chiral Amines
Abstract
Chiral amines such as (S)-2-[bis(3,5-dimethylphenyl)methyl]pyrrolidine and the C(2)-symmetric (2S,5S)-2,5-diphenylpyrrolidine can catalyze the direct enantioselective Michael addition of simple aldehydes to vinyl ketones. The conditions for this organocatalytic reaction have been optimized and it has been found that the chiral amines catalyze the formation of optically active substituted 5-keto aldehydes in good yields and enantioselectivities, using aldehydes and, e.g., methyl vinyl ketone as starting compounds. Taking into account that the chiral amine can activate the aldehyde and/or the enone, the mechanism for the reaction has been investigated. On the basis of intermediate synthesis, nonlinear effect, and theoretical investigations, the mechanism for the catalytic direct enantioselective Michael addition of aldehydes to vinyl ketones is discussed.
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Citations
Cited by
Erkkilä, A., Majander, I., & Pihko, P. M. (2007) · Chemical Reviews · doi:10.1021/cr068388p · Cited by 1,441
Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry
Melchiorre, P., Marigo, M., Carlone, A., & Bartoli, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705523 · Cited by 1,256
Self-citationFranzén, J., Marigo, M., Fielenbach, D., Wabnitz, T. C., Kjærsgaard, A., & Jørgensen, K. A. (2005) · Journal of the American Chemical Society · doi:10.1021/ja056120u · Cited by 640
Self-citationNonlinear Effects in Asymmetric Catalysis
Satyanarayana, T., Abraham, S., & Kagan, H. B. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200705241 · Cited by 591
Hoashi, Y., Okino, T., & Takemoto, Y. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200500459 · Cited by 275
Metadata
- Authors
- Melchiorre, P., & Jørgensen, K. A.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-05-01
- Volume
- 68
- Issue
- 11
- Pages
- 4151-4157
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2143870478
- Cited by
- 184
- References
- 0
- FWCI
- 10.10
- Type
- journal article
- Language
- en
- Open access
- closed
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- Melchiorre, P., & Jørgensen, K. A. (2003). Direct Enantioselective Michael Addition of Aldehydes to Vinyl Ketones Catalyzed by Chiral Amines. The Journal of Organic Chemistry. https://doi.org/10.1021/jo026837p
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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