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Enantioselective α-Arylation of Aldehydes via Organo-SOMO Catalysis. An Ortho-Selective Arylation Reaction Based on an Open-Shell Pathway
Open accessAbstract
The intramolecular alpha-arylation of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3pi-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective reaction with an array of pendent electron-rich aromatics and heterocycles thus efficiently providing cyclic alpha-aryl aldehyde products (10 examples: > or = 70% yield and > or = 90% ee). In accordance with our radical mechanism, when there is a choice between arylation at the ortho or para position of anisole substrates, we find that arylation proceeds selectively at the ortho position.
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Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Self-citationPhotoactive Chiral Metal–Organic Frameworks for Light-Driven Asymmetric α-Alkylation of Aldehydes
Wu, P., He, C., Wang, J., Peng, X., Li, X., An, Y., & Duan, C. (2012) · Journal of the American Chemical Society · doi:10.1021/ja305367j · Cited by 445
Metadata
- Authors
- Conrad, J. C., Kong, J., Laforteza, B. N., & MacMillan, D. W. C.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-07-29
- Volume
- 131
- Issue
- 33
- Pages
- 11640-11641
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2018826376
- Cited by
- 255
- References
- 0
- FWCI
- 14.69
- Type
- journal article
- Language
- en
- Open access
- green
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- Conrad, J. C., Kong, J., Laforteza, B. N., & MacMillan, D. W. C. (2009). Enantioselective α-Arylation of Aldehydes via Organo-SOMO Catalysis. An Ortho-Selective Arylation Reaction Based on an Open-Shell Pathway. Journal of the American Chemical Society. https://doi.org/10.1021/ja9026902
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