The DOI matches its Crossref record; 20 of the 20 references it cites were found in a registry or an index.
A General Organocatalyst for Direct α-Functionalization of Aldehydes: Stereoselective C−C, C−N, C−F, C−Br, and C−S Bond-Forming Reactions. Scope and Mechanistic Insights
Abstract
The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active alpha,alpha-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic formation of C-C, C-N, C-F, C-Br, and C-S bonds are outlined. The reactions all proceed in good to high yields and with excellent enantioselectivities. Furthermore, we will present mechanistic insight into the reaction course applying nonlinear effect studies, kinetic resolution, and computational investigations leading to an understanding of the properties of the alpha,alpha-diarylprolinol silyl ether catalysts.
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Cites
Proline-Catalyzed Direct Asymmetric Aldol Reactions
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In the Golden Age of Organocatalysis
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The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes
Northrup, A. B., & MacMillan, D. W. C. (2002) · Journal of the American Chemical Society · doi:10.1021/ja0262378 · Cited by 706
The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes
Brown, S. P., Brochu, M. P., Sinz, C. J., & MacMillan, D. W. C. (2003) · Journal of the American Chemical Society · doi:10.1021/ja037096s · Cited by 528
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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
Self-citationAsymmetric Organocatalysis: From Infancy to Adolescence
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200704684 · Cited by 1,252
Kobayashi, S., Mori, Y., Fossey, J. S., & Salter, M. M. (2011) · Chemical Reviews · doi:10.1021/cr100204f · Cited by 988
Monofluorination of Organic Compounds: 10 Years of Innovation
Champagne, P. A., Desroches, J., Hamel, J.-D., Vandamme, M., & Paquin, J.-F. (2015) · Chemical Reviews · doi:10.1021/cr500706a · Cited by 963
Organocatalytic Carbon–Sulfur Bond-Forming Reactions
Chauhan, P., Mahajan, S., & Enders, D. (2014) · Chemical Reviews · doi:10.1021/cr500235v · Cited by 632
Metadata
- Authors
- Franzén, J., Marigo, M., Fielenbach, D., Wabnitz, T. C., Kjærsgaard, A., & Jørgensen, K. A.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-12-01
- Volume
- 127
- Issue
- 51
- Pages
- 18296-18304
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2013092331
- Cited by
- 640
- References
- 20
- FWCI
- 24.41
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: A General Organocatalyst for Direct α-Functionalization of Aldehydes: Stereoselective C−C, C−N, C−F, C−Br, and C−S Bond-Forming Reactions. Scope and Mechanistic Insights. https://app.cochat.ai/papers/10.1021/ja056120u
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- Franzén, J., Marigo, M., Fielenbach, D., Wabnitz, T. C., Kjærsgaard, A., & Jørgensen, K. A. (2005). A General Organocatalyst for Direct α-Functionalization of Aldehydes: Stereoselective C−C, C−N, C−F, C−Br, and C−S Bond-Forming Reactions. Scope and Mechanistic Insights. Journal of the American Chemical Society. https://doi.org/10.1021/ja056120u
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