Evidence map›Paper›PMID 36929023›Full record

ArticleAngewandte Chemie (International ed. in English)2023

Diastereoselective Synthesis of Cyclopropanes from Carbon Pronucleophiles and Alkenes.

Min Ji Kim, Diana J Wang, Karina Targos, Uriel A Garcia, Alison F Harris, Ilia A Guzei, Zachary K Wickens

Open access · hybridAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.

0numbers the graph read from it
0cells of the map it votes in
18citing papers in PubMed
7.0field-weighted citation impact, top 2% of its field
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

18 citing papers in PubMed, 47 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Synthesis of 1,3-Dienes from Alkenes via Alkenyl Thianthrenium Salts.Journal of the American Chemical Society · 2026
    Article
  5. Review
  6. Enriching AlkeneOrganic letters · 2026
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  7. Article
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  10. Stereo-reversed E2 unlocksScience (New York, N.Y.) · 2025
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  12. Article
  13. Article
  14. Journal of the American Chemical Society · 2024
    Article
  15. Mechanism ofJournal of the American Chemical Society · 2024
    Article
  16. Article
  17. Review
  18. 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

7 authors at 1 institution in 1 country.

Min Ji KimDepartment of Chemistry, University of Wisconsin, Madison, Madison, WI 53706, USA.ORCID http://orcid.org/0000-0002-0542-3577
Diana J WangDepartment of Chemistry, University of Wisconsin, Madison, Madison, WI 53706, USA.ORCID http://orcid.org/0000-0003-3790-0240
Karina TargosDepartment of Chemistry, University of Wisconsin, Madison, Madison, WI 53706, USA.ORCID http://orcid.org/0000-0002-9945-0719
Uriel A GarciaDepartment of Chemistry, University of Wisconsin, Madison, Madison, WI 53706, USA.ORCID http://orcid.org/0000-0002-4138-7518
Alison F HarrisDepartment of Chemistry, University of Wisconsin, Madison, Madison, WI 53706, USA.ORCID http://orcid.org/0000-0003-1126-3351
Ilia A GuzeiDepartment of Chemistry, University of Wisconsin, Madison, Madison, WI 53706, USA.ORCID http://orcid.org/0000-0003-1976-7386
Zachary K WickensDepartment of Chemistry, University of Wisconsin, Madison, Madison, WI 53706, USA.ORCID http://orcid.org/0000-0002-5733-5288
University of Wisconsin–Madison · US

Funding

Laser-Enhanced NMR Instrumentation for Chemical and Biochemical ResearchS10OD012245 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI CAVAGNERO, SILVIA · 2013 to 2013
$1.0M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
NIH HHS S10 OD012245NIH HHS S10 OD020022
6 · The paper itself

Abstract

Cyclopropanes are desirable structural motifs with valuable applications in drug discovery and beyond. Established alkene cyclopropanation methods give rise to cyclopropanes with a limited array of substituents, are difficult to scale, or both. Herein, we disclose a new cyclopropane synthesis through the formal coupling of abundant carbon pronucleophiles and unactivated alkenes. This strategy exploits dicationic adducts derived from electrolysis of thianthrene in the presence of alkene substrates. We find that these dielectrophiles undergo cyclopropanation with methylene pronucleophiles via alkenyl thianthrenium intermediates. This protocol is scalable, proceeds with high diastereoselectivity, and tolerates diverse functional groups on both the alkene and pronucleophile coupling partners. To validate the utility of this new procedure, we prepared an array of substituted analogs of an established cyclopropane that is en route to multiple pharmaceuticals.

Indexed as

AlkeneCyclopropanationElectrochemistryOxidation

Identifiers

PMID36929023
PMCPMC10189787
OpenAlexW4327587745

What OpenQuestion holds

Textmetadata
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Registered trials

None linked

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.