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Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1 H)-Quinolones Induced by Visible Light Irradiation
Open accessAbstract
In the presence of a chiral thioxanthone catalyst (10 mol %) the title compounds underwent a clean intermolecular [2 + 2] photocycloaddition with electron-deficient olefins at λ = 419 nm. The reactions not only proceeded with excellent regio- and diastereoselectivity but also delivered the respective cyclobutane products with significant enantiomeric excess (up to 95% ee). Key to the success of the reactions is a two-point hydrogen bonding between quinolone and catalyst enabling efficient energy transfer and high enantioface differentiation. Preliminary work indicated that solar irradiation can be used for this process and that the substrate scope can be further expanded to isoquinolones.
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Citations
Cited by
Triplet Energy Transfer Photocatalysis: Unlocking the Next Level
Strieth-Kalthoff, F., & Glorius, F. (2020) · Chem · doi:10.1016/j.chempr.2020.07.010 · Cited by 650
Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transfer
Kleinmans, R., Pinkert, T., Dutta, S., Paulisch, T. O., Keum, H., Daniliuc, C. G., & Glorius, F. (2022) · Nature · doi:10.1038/s41586-022-04636-x · Cited by 455
Enantioselective photochemistry through Lewis acid–catalyzed triplet energy transfer
Blum, T. R., Miller, Z. D., Bates, D. M., Guzei, I. A., & Yoon, T. P. (2016) · Science · doi:10.1126/science.aai8228 · Cited by 420
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
- Tröster, A., Alonso, R., Bauer, A., & Bach, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-06-16
- Volume
- 138
- Issue
- 25
- Pages
- 7808-7811
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2433923815
- Cited by
- 267
- References
- 0
- FWCI
- 15.00
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Tröster, A., Alonso, R., Bauer, A., & Bach, T. (2016). Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1 H)-Quinolones Induced by Visible Light Irradiation. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.6b03221
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