Evidence map›Paper›PMID 30393576›Full record

ArticleACS catalysis2018

Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation.

Andrew J Smaligo, Sriramurthy Vardhineedi, Ohyun Kwon

Abstract read
In one paragraph

Article in ACS catalysis, 2018. 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
–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

18 citing papers in PubMed.

  1. Synthesis through C(spAccounts of chemical research · 2025
    Article
  2. Hydrodealkenylative C(spJournal of the American Chemical Society · 2025
    Article
  3. Deacylative Homolysis of Ketone C(spJournal of the American Chemical Society · 2025
    Article
  4. Article
  5. Article
  6. Hydrodealkenylative Cleavage of C(spOrganic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2024
    Article
  7. Review
  8. Article
  9. Dealkenylative Alkynylation Using Catalytic FeJournal of the American Chemical Society · 2022
    Article
  10. Phosphorus-Based Catalysis.ACS central science · 2021
    Review
  11. Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins.Angewandte Chemie (International ed. in English) · 2020
    Article
  12. Article
  13. Article
  14. Oxodealkenylative Cleavage of Alkene C(spAngewandte Chemie (International ed. in English) · 2020
    Article
  15. Article
  16. Hydrodealkenylative C(spScience (New York, N.Y.) · 2019
    Article
  17. Discussion Addendum for: Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2019
    Article
  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

3 authors.

Andrew J SmaligoDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States.
Sriramurthy VardhineediDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States.
Ohyun KwonDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States.

Funding

Phosphine-Catalyzed Annulations and Their ApplicationsR01GM071779 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI OHYUN KWON · 2006 to 2026
$5.7M
NIGMS NIH HHS R01 GM071779
6 · The paper itself

Abstract

We have prepared a previously unreported family of P-stereogenic [2.2.1] bicyclic chiral phosphines through straightforward syntheses starting from the natural product carvone. This design rationale prompted the development of an unforeseen C-dealkenylation reaction. We have applied these organocatalysts in the asymmetric syntheses of a bevy of pyrrolines, obtained in high yields and enantioselectivities, including a biologically active small molecule, efsevin.

Indexed as

annulationcarvonechiral poolenantioselectiveheterocycleorganocatalysisphosphine

Identifiers

PMID30393576
PMCPMC6208446

What OpenQuestion holds

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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.