Evidence map›Paper›PMID 40676028›Full record

ArticleNature communications2025

Atroposelective construction of axially chiral alkenylindole-fused nine-membered rings via catalytic asymmetric formal (4 + 5) cycloaddition.

Si-Jia Liu, Xue Wang, Ji-Xiang Yang, Xian-Song Ao, Shao-Fei Ni, Yu-Chen Zhang, Feng Shi

Abstract read
In one paragraph

Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing 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

8 citing papers in PubMed.

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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.

Si-Jia Liu *Research Center of Chiral Functional Heterocycles, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China.ORCID http://orcid.org/0009-0002-7195-1922
Xue Wang *Research Center of Chiral Functional Heterocycles, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China.ORCID http://orcid.org/0009-0003-6536-1309
Ji-Xiang Yang *College of Chemistry & Chemical Engineering, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou, China.ORCID http://orcid.org/0009-0009-6551-5113
Xian-Song AoResearch Center of Chiral Functional Heterocycles, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China.ORCID http://orcid.org/0009-0000-3848-706X
Shao-Fei NiCollege of Chemistry & Chemical Engineering, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou, China. sfni@stu.edu.cn.ORCID http://orcid.org/0000-0001-9860-2138
Yu-Chen ZhangResearch Center of Chiral Functional Heterocycles, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China. zhangyc@jsnu.edu.cn.ORCID http://orcid.org/0000-0002-8399-7824
Feng ShiResearch Center of Chiral Functional Heterocycles, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China. fshi@jsnu.edu.cn.ORCID http://orcid.org/0000-0003-3922-0708

Funding

Basic Research Program of Jiangsu Province BK20240052National Natural Science Foundation of China (National Science Foundation of China) 22101103National Natural Science Foundation of China (National Science Foundation of China) 22125104
6 · The paper itself

Abstract

Catalytic atroposelective construction of axially chiral aryl-fused medium-sized rings, particularly nine-membered rings, is of great importance but with enormous challenges. To overcome these challenges, in this work, the catalytic atroposelective construction of axially chiral arylalkene-fused nine-membered rings has been established, which makes use of organocatalytic asymmetric formal (4 + 5) cycloaddition of 3-alkynyl-2-indolylmethanols with 2-indolylethanols. By this strategy, various axially chiral alkenylindole-fused nine-membered rings were constructed in high enantioselectivities with moderate to good yields (up to 74% yield, 98% ee). Theoretical calculations provide an in-depth understanding on the reaction pathway and activation mode of the organocatalytic asymmetric formal (4 + 5) cycloaddition, and application explorations demonstrate the great potential of these axially chiral arylalkene-fused nine-membered rings in asymmetric catalysis and medicinal chemistry. Besides, this strategy could be extended to organocatalytic formal (4 + 4) cycloaddition of 3-alkynyl-2-indolylmethanols with 2-indolylmethanols. This work has not only realized the organocatalytic asymmetric formal (4 + 5) cycloaddition, but also provided an efficient strategy for the synthesis of axially chiral aryl-fused nine-membered rings, which will greatly advance the chemistry of cycloadditions and atropisomers.

Identifiers

PMID40676028
PMCPMC12271338

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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.