Evidence map›Paper›PMID 38648196›Full record

ArticleOrganic letters2024

Evaluation of Retro-Aldol vs Retro-Carbonyl-Ene Mechanistic Pathways in a Complexity-Generating C-C Bond Fragmentation.

Ana S Bulger, Daniel W Turner, Qingyang Zhou, K N Houk, Neil K Garg

Abstract read
In one paragraph

Article in Organic letters, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. 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

5 authors.

Ana S BulgerDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
Daniel W TurnerDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
Qingyang ZhouDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.ORCID 0000-0002-8387-5261
Neil K GargDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.ORCID 0000-0002-7793-2629

Funding

Exploiting Unconventional Building Blocks in Chemical SynthesisR35GM139593 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI Neil K. Garg · 2021 to 2026
$4.0M
Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical ResearchS10RR025631 · NCRR · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N · 2009 to 2009
$328k
NCRR NIH HHS S10 RR025631NIGMS NIH HHS R35 GM139593
6 · The paper itself

Abstract

We report an experimental and computational investigation of the likely mechanism of a cascade reaction. The reaction involves an intramolecular Diels-Alder reaction, followed by a C-C bond cleavage, to afford a complex bridged bicyclic product. As multiple reaction pathways could be envisioned for the latter step, the mechanism of the C-C bond cleavage step was investigated. Two reasonable reaction pathways were evaluated. Both computations and experiments indicate that the C-C bond cleavage step proceeds by a retro-carbonyl-ene pathway rather than a retro-aldol pathway. This report underscores the synergy between computational and experimental studies and establishes the mechanism of an interesting complexity-generating transformation.

Identifiers

PMID38648196
PMCPMC11068157

What OpenQuestion holds

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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.