The DOI matches its Crossref record; 8 of the 8 references it cites were found in a registry or an index.
Science
Open accessAbstract
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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Metadata
- Authors
- Beeson, T. D., Mastracchio, A., Hong, J.-B., Ashton, K., & MacMillan, D. W. C.
- Affiliations
- Princeton University (US)
- Corresponding author
- Teresa D Beeson
- Venue
- Science
- Published
- 2023-07-12
- Volume
- 314
- Issue
- 5803
- Pages
- 1249-5
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W1507573241
- Cited by
- 6,063
- References
- 8
- Citations by year
- 2026: 72 · 2025: 224 · 2024: 499 · 2023: 931
- Type
- paratext
- Language
- en
- Open access
- green
- research.vu.nl
- Licence
- other-oa
- Locations
- Science (publishedVersion)
- PubMed (publishedVersion)
- VU Research Portal (publishedVersion, other-oa)
- CaltechAUTHORS (California Institute of Technology) (submittedVersion)
- Max Planck Institute for Plasma Physics (submittedVersion)
- Publication Database GFZ (GFZ German Research Centre for Geosciences) (submittedVersion)
- Iris (Roma Tre University) (submittedVersion)
- Institutional Research Information System University of Turin (University of Turin) (submittedVersion)
- CNR ExploRA (submittedVersion)
- ANU Open Research (Australian National University) (submittedVersion)
- MPG.PuRe (Max Planck Society) (submittedVersion)
- Data Archiving and Networked Services (DANS) (submittedVersion, other-oa)
- PubMed
- Funders
- National Institutes of Health (2r01gm078201-13)
- Japan Society for the Promotion of Science (21229007, 21113002)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Radical Photochemical Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Keywords
- α-allylation, aldehydes, ketones, chiral amine catalysis, enamine formation, one-electron oxidation
- MeSH terms
- Brain, Brain Mapping, Energy Metabolism, Humans, Magnetic Resonance Imaging, Mental Processes, Neural Pathways, Neurons, Oxygen, Synapses
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- CoChat. (2026). Citation check: Science. https://app.cochat.ai/papers/10.1126/science
- The paper
- Beeson, T. D., Mastracchio, A., Hong, J.-B., Ashton, K., & MacMillan, D. W. C. (2023). Science. Science. https://doi.org/10.1126/science
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.