Evidence map›Paper›PMID 36480623›Full record

ArticleScience (New York, N.Y.)2022

Catalytic asymmetric C-H insertion reactions of vinyl carbocations.

Sepand K Nistanaki, Chloe G Williams, Benjamin Wigman, Jonathan J Wong, Brittany C Haas, Stasik Popov, Jacob Werth, Matthew S Sigman, K N Houk, Hosea M Nelson

Abstract read
In one paragraph

Article in Science (New York, N.Y.), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.

0numbers the graph read from it
0cells of the map it votes in
20citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

20 citing papers in PubMed.

  1. Catalytic Asymmetric Hydration of Alkenes.Journal of the American Chemical Society · 2026
    Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. Article
  8. Review
  9. Article
  10. Article
  11. Article
  12. Rh-Catalyzed Enantioselective Single-Carbon Insertion of Alkenes.Journal of the American Chemical Society · 2024
    Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

10 authors.

Sepand K NistanakiDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0002-5252-803X
Chloe G WilliamsDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0001-5090-8146
Benjamin WigmanDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA.ORCID 0000-0003-3689-8281
Jonathan J WongDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA.ORCID 0000-0002-6656-5421
Brittany C HaasDepartment of Chemistry, University of Utah, Salt Lake City, UT 84112, USA.ORCID 0000-0001-5344-4375
Stasik PopovDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA.ORCID 0000-0002-8870-0807
Jacob WerthDepartment of Chemistry, University of Utah, Salt Lake City, UT 84112, USA.ORCID 0000-0001-9648-5986
Matthew S SigmanDepartment of Chemistry, University of Utah, Salt Lake City, UT 84112, USA.ORCID 0000-0002-5746-8830
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA.ORCID 0000-0002-8387-5261
Hosea M NelsonDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.ORCID 0000-0002-4666-2793

Funding

CHEMISTRY BIOLOGY INTERFACE TRAINING PROGRAMT32GM008496 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI MAYNARD, HEATHER D · 1993 to 2019
$6.3M
Data Science Guided Organic Reaction DevelopmentR35GM136271 · NIGMS · UTAH STATE HIGHER EDUCATION SYSTEM--UNIVERSITY OF UTAH · PI MATTHEW S SIGMAN · 2020 to 2026
$3.5M
NIGMS NIH HHS R35 GM136271NIGMS NIH HHS T32 GM008496
6 · The paper itself

Abstract

From the preparation of pharmaceuticals to enzymatic construction of natural products, carbocations are central to molecular synthesis. Although these reactive intermediates are engaged in stereoselective processes in nature, exerting enantiocontrol over carbocations with synthetic catalysts remains challenging. Many resonance-stabilized tricoordinated carbocations, such as iminium and oxocarbenium ions, have been applied in catalytic enantioselective reactions. However, their dicoordinated counterparts (aryl and vinyl carbocations) have not, despite their emerging utility in chemical synthesis. We report the discovery of a highly enantioselective vinyl carbocation carbon-hydrogen (C-H) insertion reaction enabled by imidodiphosphorimidate organocatalysts. Active site confinement featured in this catalyst class not only enables effective enantiocontrol but also expands the scope of vinyl cation C-H insertion chemistry, which broadens the utility of this transition metal-free C(sp

Identifiers

PMID36480623
PMCPMC9993429

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.