Evidence map›Paper›PMID 37712017›Full record

ArticleChemical science2023

Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction.

Yu Hao, Zi-Hao Li, Zhi-Gang Ma, Ru-Xin Liu, Rui-Tian Ge, Quan-Zhe Li, Tong-Mei Ding, Shu-Yu Zhang

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing 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

1 citing paper in PubMed.

  1. 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

8 authors.

Yu HaoShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China zhangsy16@sjtu.edu.cn.
Zi-Hao LiShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China zhangsy16@sjtu.edu.cn.
Zhi-Gang MaShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China zhangsy16@sjtu.edu.cn.
Ru-Xin LiuShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China zhangsy16@sjtu.edu.cn.
Rui-Tian GeShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China zhangsy16@sjtu.edu.cn.
Quan-Zhe LiShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China zhangsy16@sjtu.edu.cn.
Tong-Mei DingShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China zhangsy16@sjtu.edu.cn.
Shu-Yu ZhangShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China zhangsy16@sjtu.edu.cn.ORCID https://orcid.org/0000-0002-1811-4159

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

An axially chiral styrene-based organocatalyst, featuring a combination of axially chiral styrene-based structure and a pyrrole ring, has been designed and synthesized. This catalyst demonstrates remarkable capabilities in producing a wide range of densely substituted spirooxindoles that feature an alkyne-substituted quaternary stereogenic center. These spirooxindoles are generated through mild cascade Michael/cyclization reactions, resulting in high conversion rates and exceptional enantioselectivity. Our catalytic model, based on experiments, X-ray structure analysis and DFT calculations suggests that chiral matched π-π interactions and multiple H-bonds between the organocatalyst and substrates play significant roles in controlling the stereoselectivity of the reaction.

Identifiers

PMID37712017
PMCPMC10498726

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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.