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Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines
Abstract
A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.
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Cited by
Mechanisms of Nickel-Catalyzed Cross-Coupling Reactions
Diccianni, J. B., & Diao, T. (2019) · Trends in Chemistry · doi:10.1016/j.trechm.2019.08.004 · Cited by 584
Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis
Ehehalt, L. E., Beleh, O. M., Priest, I. C., Mouat, J. M., Olszewski, A. K., Ahern, B. N., Cruz, A. R., Chi, B. K., Castro, A. J., Kang, K., et al. (2024) · Chemical Reviews · doi:10.1021/acs.chemrev.4c00524 · Cited by 312
Stereospecific and stereoconvergent cross-couplings between alkyl electrophiles
Lucas, E. L., & Jarvo, E. R. (2017) · Nature Reviews Chemistry · doi:10.1038/s41570-017-0065 · Cited by 300
Zahrt, A. F., Athavale, S. V., & Denmark, S. E. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00425 · Cited by 212
Machine Learning Approach for Prediction of Reaction Yield with Simulated Catalyst Parameters
Yada, A., Nagata, K., Ando, Y., Matsumura, T., Ichinoseki, S., & Sato, K. (2018) · Chemistry Letters · doi:10.1246/cl.171130 · Cited by 67
Metadata
- Authors
- Woods, B. P., Orlandi, M., Huang, C.-Y., Sigman, M. S., & Doyle, A. G.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-04-13
- Volume
- 139
- Issue
- 16
- Pages
- 5688-5691
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2606353208
- Cited by
- 296
- References
- 0
- FWCI
- 11.39
- Type
- journal article
- Language
- en
- Open access
- closed
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- Woods, B. P., Orlandi, M., Huang, C.-Y., Sigman, M. S., & Doyle, A. G. (2017). Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.7b03448
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