Cited by 6,063Asymmetric Synthesis and CatalysisRadical Photochemical ReactionsOxidative Organic Chemistry Reactions

Science

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Teresa D Beeson, Anthony Mastracchio, Jun-Bae Hong, Kate Ashton, David W. C. MacMillan·2023·Science

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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Crossref · 10.1126/science

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  • More recent studies support a basal position for the ctenophore clade.

    “more recent studies have attempt to resolve these difficulties and support a basal position for the clade [4,5,11]”

    From Early metazoan life: divergence, environment and ecology (2015) · cites this paper as [4]

  • Neural activity during REM sleep can be modulated by prior wake experience and there have been occasional reports of reactivation-like phenomena in REM sleep.

    “neural activity during REM sleep can be modulated by prior wake experience 106,134 and there have been occasional reports of reactivation-like phenomena in REM sleep.”

    From Sleep—A brain-state serving systems memory consolidation (2023) · cites this paper as [134]

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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
2
Citations by year
2026: 72 · 2025: 224 · 2024: 499 · 2023: 931 · 2022: 758 · 2021: 711 · 2020: 581 · 2019: 346 · 2018: 234 · 2017: 199 · 2016: 217 · 2015: 216 · 2014: 198 · 2013: 563 · 2012: 66
Type
paratext
Language
en
Open access
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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