Evidence map›Paper›PMID 31692203›Full record

ArticleAngewandte Chemie (International ed. in English)2020

Oxodealkenylative Cleavage of Alkene C(sp

Andrew J Smaligo, Jason Wu, Nikolas R Burton, Allison S Hacker, Aslam C Shaikh, Jason C Quintana, Ruoxi Wang, Changmin Xie, Ohyun Kwon

Open access · greenAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.

0numbers the graph read from it
0cells of the map it votes in
17citing papers in PubMed
2.1field-weighted citation impact, top 14% 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

17 citing papers in PubMed, 35 citations in OpenAlex.

  1. Review
  2. Iron-Catalyzed Dealkenylative Borylation of Alkenes via Ozonolysis.Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Article
  5. Synthesis through C(spAccounts of chemical research · 2025
    Article
  6. Hydrodealkenylative C(spJournal of the American Chemical Society · 2025
    Article
  7. Article
  8. Article
  9. Oxoammonium-Catalyzed Oxidation ofJournal of the American Chemical Society · 2024
    Article
  10. Hydrodealkenylative Cleavage of C(spOrganic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2024
    Article
  11. Article
  12. When all C-C breaks LO-Ose.Trends in chemistry · 2023
    Article
  13. Dealkenylative Alkynylation Using Catalytic FeJournal of the American Chemical Society · 2022
    Article
  14. Article
  15. Article
  16. C-H Insertion via Ruthenium CatalyzedJournal of the American Chemical Society · 2022
    Article
  17. Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins.Angewandte Chemie (International ed. in English) · 2020
    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

9 authors at 1 institution in 1 country.

Andrew J SmaligoDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.ORCID http://orcid.org/0000-0003-3329-022X
Jason WuDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Nikolas R BurtonDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Allison S HackerDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Aslam C ShaikhDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Jason C QuintanaDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Ruoxi WangDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Changmin XieDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Ohyun KwonDepartment of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.ORCID http://orcid.org/0000-0002-5405-3971
University of California, Los Angeles · US

Funding

Phosphine-Catalyzed Annulations and Their ApplicationsR01GM071779 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI OHYUN KWON · 2006 to 2026
$5.7M
Deconstructive Molecular Editing Technology Involving C-C Bond ScissionR01GM141327 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI KWON, OHYUN · 2021 to 2024
$1.4M
NIGMS NIH HHS R01 GM071779NIGMS NIH HHS R01 GM141327NIH HHS R01GM071779
6 · The paper itself

Abstract

Reported herein is a one-pot protocol for the oxodealkenylative introduction of carbonyl functionalities into terpenes and terpene-derived compounds. This transformation proceeds by Criegee ozonolysis of an alkene, reductive cleavage of the resulting α-alkoxy hydroperoxide, trapping of the generated alkyl radical with 2,2,6,6-tetramethylpiperidin-1-yl (TEMPO), and subsequent oxidative fragmentation with MMPP. Using readily available starting materials from chiral pool, a variety of carbonyl-containing products have been accessed rapidly in good yields.

Indexed as

alkenesoxidationozonolysisradicalsterpenoids

Identifiers

PMID31692203
PMCPMC6942233
OpenAlexW2986212427

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

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.