Evidence map›Paper›PMID 38485991›Full record

ArticleNature communications2024

Valence-isomer selective cycloaddition reaction of cycloheptatrienes-norcaradienes.

Shingo Harada, Hiroki Takenaka, Tsubasa Ito, Haruki Kanda, Tetsuhiro Nemoto

Abstract read
In one paragraph

Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Copper-Catalyzed DearomativeACS catalysis · 2024
    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.

Shingo HaradaGraduate School of Pharmaceutical Sciences, Chiba University, Chiba, 260-8675, Japan. Sharada@chiba-u.jp.ORCID http://orcid.org/0000-0002-8373-4143
Hiroki Takenaka *Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, 260-8675, Japan.
Tsubasa Ito *Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, 260-8675, Japan.
Haruki KandaGraduate School of Pharmaceutical Sciences, Chiba University, Chiba, 260-8675, Japan.
Tetsuhiro NemotoGraduate School of Pharmaceutical Sciences, Chiba University, Chiba, 260-8675, Japan. tnemoto@faculty.chiba-u.jp.ORCID http://orcid.org/0000-0001-8858-161X

Funding

Futaba Electronics Memorial Foundation 223014MEXT | Japan Society for the Promotion of Science (JSPS) 22H02741MEXT | Japan Society for the Promotion of Science (JSPS) 22KJ0470Sumitomo Foundation 210318Takeda Science Foundation 2023077185
6 · The paper itself

Abstract

The rapid and precise creation of complex molecules while controlling multiple selectivities is the principal objective in synthetic chemistry. Combining data science and organic synthesis to achieve this goal is an emerging trend, but few examples of successful reaction designs are reported. We develop an artificial neural network regression model using bond orbital data to predict chemical reactivities. Actual experimental verification confirms cycloheptatriene-selective [6 + 2]-cycloaddition utilizing nitroso compounds and norcaradiene-selective [4 + 2]-cycloaddition reactions employing benzynes. Additionally, a one-pot asymmetric synthesis is achieved by telescoping the enantioselective dearomatization of non-activated benzenes and cycloadditions. Computational studies provide a rational explanation for the seemingly anomalous occurrence of thermally prohibited suprafacial [6 + 2]-cycloaddition without photoirradiation.

Identifiers

PMID38485991
PMCPMC10940685

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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.