The DOI matches its Crossref record; 29 of the 29 references it cites were found in a registry or an index.
Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations
Abstract
A combination of NHC organocatalysis and transition-metal catalysis gives rise to fundamentally new cooperative reactivity and enables the regio- and enantioselective annulation reaction between enals and vinyl benzoxazinanones. The cooperative umpolung annulation eliminates mutual deactivation and leads to a diverse set of benzazepine derivatives in good yields with excellent enantioselectivities (up to 99% ee). The development of such a cooperative catalytic system dramatically expands the scope of NHC organocatalysis by opening up new metal-catalyzed reaction pathways for homoenolate intermediates.
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Cites
An overview of N-heterocyclic carbenes
Hopkinson, M. N., Richter, C., Schedler, M., & Glorius, F. (2014) · Nature · doi:10.1038/nature13384 · Cited by 4,264
Self-citationAsymmetric Transition Metal-Catalyzed Allylic Alkylations
Trost, B. M., & Vranken, D. L. V. (1996) · Chemical Reviews · doi:10.1021/cr9409804 · Cited by 3,205
N-Heterocyclic Carbenes in Late Transition Metal Catalysis
Díez-González, S., Marion, N., & Nolan, S. P. (2009) · Chemical Reviews · doi:10.1021/cr900074m · Cited by 3,066
Organocatalysis by N-Heterocyclic Carbenes
Enders, D., Niemeier, O., & Henseler, A. (2007) · Chemical Reviews · doi:10.1021/cr068372z · Cited by 3,059
Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total Synthesis
Trost, B. M., & Crawley, M. L. (2003) · Chemical Reviews · doi:10.1021/cr020027w · Cited by 2,845
Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes
Nicewicz, D. A., & MacMillan, D. W. C. (2008) · Science · doi:10.1126/science.1161976 · Cited by 2,489
Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes
Flanigan, D. M., Romanov-Michailidis, F., White, N. A., & Rovis, T. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00060 · Cited by 2,045
N‐Heterocyclic Carbenes as Organocatalysts
Marion, N., Díez‐González, S., & Nolan, S. P. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200603380 · Cited by 1,459
Organocatalytic umpolung: N-heterocyclic carbenes and beyond
Bugaut, X., & Glorius, F. (2012) · Chemical Society Reviews · doi:10.1039/c2cs15333e · Cited by 1,394
Self-citationFortman, G. C., & Nolan, S. P. (2011) · Chemical Society Reviews · doi:10.1039/c1cs15088j · Cited by 1,258
Metadata
- Authors
- Guo, C., Fleige, M., Janssen-Müller, D., Daniliuc, C. G., & Glorius, F.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-06-15
- Volume
- 138
- Issue
- 25
- Pages
- 7840-7843
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2412361205
- Cited by
- 344
- References
- 29
- FWCI
- 19.01
- Type
- journal article
- Language
- en
- Open access
- closed
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- Guo, C., Fleige, M., Janssen-Müller, D., Daniliuc, C. G., & Glorius, F. (2016). Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.6b04364
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