The DOI matches its Crossref record; 6 of the 6 references it cites were found in a registry or an index.
Enantioselective Organocatalysis Using SOMO Activation
Abstract
The asymmetric α-addition of relatively nonpolar hydrocarbon substrates, such as allyl and aryl groups, to aldehydes and ketones remains a largely unsolved problem in organic synthesis, despite the wide potential utility of direct routes to such products. We reasoned that well-established chiral amine catalysis, which activates aldehydes toward electrophile addition by enamine formation, could be expanded to this important reaction class by applying a single-electron oxidant to create a transient radical species from the enamine. We demonstrated the concept of singly occupied molecular orbital (SOMO) activation with a highly selective α-allylation of aldehydes, and we here present preliminary results for enantioselective heteroarylations and cyclization/halogenation cascades.
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Cites
Proline-Catalyzed Direct Asymmetric Aldol Reactions
List, B., Lerner, R. A., & Barbas, C. F. (2000) · Journal of the American Chemical Society · doi:10.1021/ja994280y · Cited by 2,873
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
Asymmetric Catalysis by Chiral Hydrogen‐Bond Donors
Taylor, M. S., & Jacobsen, E. N. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200503132 · Cited by 1,906
Ahrendt, K. A., Borths, C. J., & MacMillan, D. W. C. (2000) · Journal of the American Chemical Society · doi:10.1021/ja000092s · Cited by 1,701
Self-citationThe Organometallic Chemistry of the Transition Metals
Crabtree, R. H. (2005) · Wiley eBooks · doi:10.1002/0471718769 · Cited by 835
Organocatalysis in Radical Chemistry. Enantioselective α-Oxyamination of Aldehydes
Sibi, M. P., & Hasegawa, M. (2007) · Journal of the American Chemical Society · doi:10.1021/ja069245n · Cited by 301
Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Self-citationAsymmetric Aminocatalysis—Gold Rush in Organic Chemistry
Melchiorre, P., Marigo, M., Carlone, A., & Bartoli, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705523 · Cited by 1,256
Asymmetrische Organokatalyse: Eintritt in die Reifezeit
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie · doi:10.1002/ange.200704684 · Cited by 398
Metadata
- Authors
- Beeson, T. D., Mastracchio, A., Hong, J.-B., Ashton, K., & MacMillan, D. W. C.
- Venue
- Science
- Published
- 2007-04-27
- Volume
- 316
- Issue
- 5824
- Pages
- 582-585
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2972991031
- Cited by
- 518
- References
- 6
- FWCI
- 16.80
- Type
- journal article
- Language
- en
- Open access
- closed
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- Beeson, T. D., Mastracchio, A., Hong, J.-B., Ashton, K., & MacMillan, D. W. C. (2007). Enantioselective Organocatalysis Using SOMO Activation. Science. https://doi.org/10.1126/science.1142696
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