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Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation
Abstract
A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. Therefore, the substrate scope is not limited in benzoxazinones; the biomimetic asymmetric hydrogenation of benzoxazines, quinoxalines, and quinolines also gives excellent activities and enantioselectivities. Meanwhile, an unexpected reversal of enantioselectivity was observed between the reactions promoted by the different NAD(P)H models, which is ascribed to the different hydride transfer pathway.
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Cites
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Houtkooper, R. H., Cantó, C., Wanders, R. J., & Auwerx, J. (2010) · Endocrine Reviews · doi:10.1210/er.2009-0026 · Cited by 899
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Parmar, D., Sugiono, E., Raja, S., & Rueping, M. (2014) · Chemical Reviews · doi:10.1021/cr5001496 · Cited by 2,118
Combining transition metal catalysis and organocatalysis – an update
Du, Z., & Shao, Z. (2013) · Chem. Soc. Rev. · doi:10.1039/c2cs35258c · Cited by 706
Cabré, A., Verdaguer, X., & Riera, A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00496 · Cited by 477
Selective Arene Hydrogenation for Direct Access to Saturated Carbo‐ and Heterocycles
Wiesenfeldt, M. P., Nairoukh, Z., Dalton, T., & Glorius, F. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201814471 · Cited by 326
Metadata
- Authors
- Chen, Q.-A., Gao, K., Duan, Y., Ye, Z.-S., Shi, L., Yang, Y., & Zhou, Y.-G.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-01-17
- Volume
- 134
- Issue
- 4
- Pages
- 2442-2448
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2134437779
- Cited by
- 272
- References
- 1
- FWCI
- 18.88
- Type
- journal article
- Language
- en
- Open access
- closed
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