The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron Transfer: Development of an Asymmetric Aza-Pinacol Cyclization
Abstract
The first highly enantioselective catalytic protocol for the reductive coupling of ketones and hydrazones is reported. These reactions proceed through neutral ketyl radical intermediates generated via a concerted proton-coupled electron transfer (PCET) event jointly mediated by a chiral phosphoric acid catalyst and the photoredox catalyst Ir(ppy)2(dtbpy)PF6. Remarkably, these neutral ketyl radicals appear to remain H-bonded to the chiral conjugate base of the Brønsted acid during the course of a subsequent C-C bond-forming step, furnishing syn 1,2-amino alcohol derivatives with excellent levels of diastereo- and enantioselectivity. This work provides the first demonstration of the feasibility and potential benefits of concerted PCET activation in asymmetric catalysis.
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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
Stubbe, J., Nocera, D. G., Yee, C. S., & Chang, M. C. Y. (2003) · Chemical Reviews · doi:10.1021/cr020421u · Cited by 823
Reece, S. Y., Hodgkiss, J. M., Stubbe, J., & Nocera, D. G. (2006) · Philosophical Transactions of the Royal Society B: Biological Sciences · doi:10.1098/rstb.2006.1874 · Cited by 294
Cited by
Parmar, D., Sugiono, E., Raja, S., & Rueping, M. (2014) · Chemical Reviews · doi:10.1021/cr5001496 · Cited by 2,118
Synthetic Applications of Proton-Coupled Electron Transfer
Gentry, E. C., & Knowles, R. R. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00272 · Cited by 773
Self-citationYin, 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
- Rono, L. J., Yayla, H. G., Wang, D. Y., Armstrong, M. F., & Knowles, R. R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-11-13
- Volume
- 135
- Issue
- 47
- Pages
- 17735-17738
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2322631918
- Cited by
- 467
- References
- 3
- FWCI
- 13.56
- Type
- journal article
- Language
- en
- Open access
- closed
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