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The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes
Abstract
The first direct enantioselective catalytic alpha-oxidation of carbonyls has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective oxyamination of aldehydes, to generate alpha-oxyaldehydes, important chiral synthons for natural product and medicinal agent synthesis. The use of l-proline as the asymmetric catalyst has been found to mediate the oxidation of a large variety of aldehyde substrates with nitrosobenzene serving as the electrophilic oxidant. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 2 mol % were generally employed in this study, successful oxidations conducted using catalyst loadings as low as 0.5 mol % are described.
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Cited by
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
Asymmetric Organocatalysis: From Infancy to Adolescence
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200704684 · Cited by 1,252
Franzén, 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
Albrecht, Ł., Jiang, H., & Jørgensen, K. A. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102522 · Cited by 466
Asymmetrische Organokatalyse: Eintritt in die Reifezeit
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie · doi:10.1002/ange.200704684 · Cited by 398
Metadata
- Authors
- Brown, S. P., Brochu, M. P., Sinz, C. J., & MacMillan, D. W. C.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-08-19
- Volume
- 125
- Issue
- 36
- Pages
- 10808-10809
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2046809701
- Cited by
- 528
- References
- 0
- FWCI
- 27.00
- Type
- journal article
- Language
- en
- Open access
- closed
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- Brown, S. P., Brochu, M. P., Sinz, C. J., & MacMillan, D. W. C. (2003). The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes. Journal of the American Chemical Society. https://doi.org/10.1021/ja037096s
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