Evidence map›Paper›PMID 39027277›Full record

ArticleChemical science2024

Synthesis of constrained bicycloalkanes through bibase-promoted brook rearrangement/radical-polar crossover cyclization.

Xinke Ouyang, Bingyao Shi, Yuanyuan Zhao, Zhimin Zhu, Ziyang Li, Yuxin Yang, Chao Shu

Abstract read
In one paragraph

Article in Chemical science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Article
  2. 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

7 authors.

Xinke OuyangState Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University (CCNU) 152 Luoyu Road Wuhan Hubei 430079 China chaoshu@ccnu.edu.cn.
Bingyao ShiState Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University (CCNU) 152 Luoyu Road Wuhan Hubei 430079 China chaoshu@ccnu.edu.cn.
Yuanyuan ZhaoState Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University (CCNU) 152 Luoyu Road Wuhan Hubei 430079 China chaoshu@ccnu.edu.cn.
Zhimin ZhuState Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University (CCNU) 152 Luoyu Road Wuhan Hubei 430079 China chaoshu@ccnu.edu.cn.
Ziyang LiState Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University (CCNU) 152 Luoyu Road Wuhan Hubei 430079 China chaoshu@ccnu.edu.cn.
Yuxin YangState Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University (CCNU) 152 Luoyu Road Wuhan Hubei 430079 China chaoshu@ccnu.edu.cn.
Chao ShuState Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University (CCNU) 152 Luoyu Road Wuhan Hubei 430079 China chaoshu@ccnu.edu.cn.ORCID https://orcid.org/0000-0002-4722-2714

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Highly constrained bicyclic scaffolds are ubiquitous and attracting increasing interest in pharmaceutical and biotechnology discoveries owing to the enhanced activities. Herein, we report a protocol to access highly substituted constrained bicycloalkanes from readily accessible α-silyl alcohols and olefins through a bibase-promoted Brook rearrangement/radical-polar crossover cyclization (RPCC) process. Of note, the practical procedure features broad substrate scope and good group tolerance under mild and operationally simple conditions, using an inexpensive organic photocatalyst. Gram-scale preparation and diverse synthetic transformations demonstrate opportunities to rapidly construct molecular complexity. Mechanistic studies have indicated that the transformation involves a bibase-promoted radical transfer rearrangement addition/radical-polar crossover cyclization relay sequence, which differs from traditional solitary RPCC reactions.

Identifiers

PMID39027277
PMCPMC11253123

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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.