The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Catalytic Asymmetric C−H Functionalization under Photoredox Conditions by Radical Translocation and Stereocontrolled Alkene Addition
Abstract
This work demonstrates how photoredox‐mediated C(sp 3)−H activation through radical translocation can be combined with asymmetric catalysis. Upon irradiation with visible light, α,β‐unsaturated N‐acylpyrazoles react with N‐alkoxyphthalimides in the presence of a rhodium‐based chiral Lewis acid catalyst and the photosensitizer fac‐[Ir(ppy)3] to provide a C−C bond‐formation product with high enantioselectivity (up to 97 % ee) and, where applicable, with some diastereoselectivity (3.0:1 d.r.). Mechanistically, the synthetic strategy exploits a radical translocation (1,5‐hydrogen transfer) from an oxygen‐centered to a carbon‐centered radical with a subsequent stereocontrolled radical alkene addition.
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Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Cited by
Ravelli, D., Fagnoni, M., Fukuyama, T., Nishikawa, T., & Ryu, I. (2018) · ACS Catalysis · doi:10.1021/acscatal.7b03354 · Cited by 533
Yin, Y., Dai, Y., Jia, H., Li, J., Bu, L., Qiao, B., Zhao, X., & Jiang, Z. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b01575 · Cited by 312
Metadata
- Authors
- Wang, C., Harms, K., & Meggers, E.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2016-09-26
- Volume
- 55
- Issue
- 43
- Pages
- 13495-13498
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2526888048
- Cited by
- 269
- References
- 1
- FWCI
- 20.19
- Type
- journal article
- Language
- en
- Open access
- closed
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- Wang, C., Harms, K., & Meggers, E. (2016). Catalytic Asymmetric C−H Functionalization under Photoredox Conditions by Radical Translocation and Stereocontrolled Alkene Addition. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201607305
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