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Catalytic Asymmetric Dearomatization by Visible‐Light‐Activated [2+2] Photocycloaddition
Abstract
A novel method for the catalytic asymmetric dearomatization by visible‐light‐activated [2+2] photocycloaddition with benzofurans and one example of a benzothiophene is reported, thereby providing chiral tricyclic structures with up to four stereocenters including quaternary stereocenters. The benzofurans and the benzothiophene are functionalized at the 2‐position with a chelating N‐acylpyrazole moiety which permits the coordination of a visible‐light‐activatable chiral‐at‐rhodium Lewis acid catalyst. Computational molecular modeling revealed the origin of the unusual regioselectivity and identified the heteroatom in the heterocycle to be key for the regiocontrol.
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Cites
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Cited by
Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis
Genzink, M. J., Kidd, J. B., Swords, W. B., & Yoon, T. P. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00467 · Cited by 420
Zhu, M., Zheng, C., Zhang, X., & You, S.-L. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.8b12965 · Cited by 298
Metadata
- Authors
- Hu, N., Jung, H., Zheng, Y., Lee, J., Zhang, L., Ullah, Z., Xie, X., Harms, K., Baik, M., & Meggers, E.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2018-04-27
- Volume
- 57
- Issue
- 21
- Pages
- 6242-6246
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2796153668
- Cited by
- 227
- References
- 1
- FWCI
- 9.19
- Type
- journal article
- Language
- en
- Open access
- closed
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- The paper
- Hu, N., Jung, H., Zheng, Y., Lee, J., Zhang, L., Ullah, Z., Xie, X., Harms, K., Baik, M., & Meggers, E. (2018). Catalytic Asymmetric Dearomatization by Visible‐Light‐Activated [2+2] Photocycloaddition. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201802891
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