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Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis
Open accessAbstract
The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity. The utility of this methodology has been demonstrated via rapid access to an enantioenriched drug target for angiogenesis suppression.
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Citations
Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Self-citationControl of a Living Radical Polymerization of Methacrylates by Light
Fors, B. P., & Hawker, C. J. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201203639 · Cited by 820
You, Y., & Nam, W. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35171d · Cited by 668
Photoactive 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
Zou, Y., Lu, L., Fu, L., Chang, N., Rong, J., Chen, J., & Xiao, W. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102306 · Cited by 435
Metadata
- Authors
- Shih, H.-W., Vander Wal, M. N., Grange, R. L., & MacMillan, D. W. C.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-09-10
- Volume
- 132
- Issue
- 39
- Pages
- 13600-13603
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1996259344
- Cited by
- 509
- References
- 0
- FWCI
- 27.31
- Type
- journal article
- Language
- en
- Open access
- green
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- Shih, H.-W., Vander Wal, M. N., Grange, R. L., & MacMillan, D. W. C. (2010). Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis. Journal of the American Chemical Society. https://doi.org/10.1021/ja106593m
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
