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The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of β-Amino Acids
Open accessAbstract
We describe the first efficient, direct asymmetric Mannich reactions with malonates and N-Boc aryl and alkyl imines by cooperative hydrogen-bonding catalysis with a cinchona alkaloid bearing a thiourea functionality. We have also extended the scope of this reaction to beta-ketoesters. The synthetic value of this new reaction is demonstrated in the establishment of a convergent enantioselective route toward the biologically important beta-amino acids under mild and air- and moisture-tolerant conditions.
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Citations
Cited by
Kobayashi, S., Mori, Y., Fossey, J. S., & Salter, M. M. (2011) · Chemical Reviews · doi:10.1021/cr100204f · Cited by 988
Cupreines and Cupreidines: An Emerging Class of Bifunctional Cinchona Organocatalysts
Marcelli, T., van Maarseveen, J. H., & Hiemstra, H. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200602318 · Cited by 353
Bui, T., Syed, S., & Barbas, C. F. (2009) · Journal of the American Chemical Society · doi:10.1021/ja903520c · Cited by 351
Zhu, J.-B., & Chen, E. Y.-X. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b08658 · Cited by 173
Metadata
- Authors
- Song, J., Wang, Y., & Deng, L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-04-18
- Volume
- 128
- Issue
- 18
- Pages
- 6048-6049
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2124218271
- Cited by
- 322
- References
- 0
- FWCI
- 24.73
- Type
- journal article
- Language
- en
- Open access
- green
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- Song, J., Wang, Y., & Deng, L. (2006). The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of β-Amino Acids. Journal of the American Chemical Society. https://doi.org/10.1021/ja060716f
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