The DOI matches its Crossref record; 26 of the 26 references it cites were found in a registry or an index.
Enantioselective photochemistry through Lewis acid–catalyzed triplet energy transfer
Open accessAbstract
Relatively few catalytic systems are able to control the stereochemistry of electronically excited organic intermediates. Here we report the discovery that a chiral Lewis acid complex can catalyze triplet energy transfer from an electronically excited photosensitizer. We applied this strategy to asymmetric [2 + 2] photocycloadditions of 2′-hydroxychalcones, using tris(bipyridyl) ruthenium(II) as a sensitizer. A variety of electrochemical, computational, and spectroscopic data rule out substrate activation by means of photoinduced electron transfer and instead support a mechanism in which Lewis acid coordination dramatically lowers the triplet energy of the chalcone substrate. We expect that this approach will enable chemists to more broadly apply their detailed understanding of chiral Lewis acid catalysis to stereocontrol in reactions involving electronically excited states.
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Cites
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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
New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry
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Zhu, M., Zheng, C., Zhang, X., & You, S.-L. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.8b12965 · Cited by 298
Ahuja, S., Jockusch, S., Ugrinov, A., & Sivaguru, J. (2020) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201901157 · Cited by 21
Metadata
- Authors
- Blum, T. R., Miller, Z. D., Bates, D. M., Guzei, I. A., & Yoon, T. P.
- Venue
- Science
- Published
- 2016-12-16
- Volume
- 354
- Issue
- 6318
- Pages
- 1391-1395
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2561089820
- Cited by
- 420
- References
- 26
- FWCI
- 17.23
- Type
- journal article
- Language
- en
- Open access
- green
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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.