Evidence map›Paper›PMID 37063803›Full record

ArticleChemical science2023

Enantio- and diastereodivergent synthesis of fused indolizines enabled by synergistic Cu/Ir catalysis.

Bing-Ke Zhu, Hui Xu, Lu Xiao, Xin Chang, Liang Wei, Huailong Teng, Yanfeng Dang, Xiu-Qin Dong, Chun-Jiang Wang

Open access · diamondAbstract read
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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 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing papers in PubMed
4.0field-weighted citation impact, top 5% of its field
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

7 citing papers in PubMed, 27 citations in OpenAlex.

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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

9 authors at 3 institutions in 1 country.

Bing-Ke ZhuCollege of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University Wuhan Hubei 430072 P. R. China xiuqindong@whu.edu.cn cjwang@whu.edu.cn.
Hui XuTianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University Tianjin 300072 China yanfeng.dang@tju.edu.cn.
Lu XiaoCollege of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University Wuhan Hubei 430072 P. R. China xiuqindong@whu.edu.cn cjwang@whu.edu.cn.
Xin ChangCollege of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University Wuhan Hubei 430072 P. R. China xiuqindong@whu.edu.cn cjwang@whu.edu.cn.
Liang WeiCollege of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University Wuhan Hubei 430072 P. R. China xiuqindong@whu.edu.cn cjwang@whu.edu.cn.ORCID https://orcid.org/0000-0002-6818-3371
Huailong TengCollege of Science, Huazhong Agricultural University Wuhan 430070 P. R. China.ORCID https://orcid.org/0000-0001-7544-2856
Yanfeng DangTianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University Tianjin 300072 China yanfeng.dang@tju.edu.cn.ORCID https://orcid.org/0000-0002-9297-9759
Xiu-Qin DongCollege of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University Wuhan Hubei 430072 P. R. China xiuqindong@whu.edu.cn cjwang@whu.edu.cn.ORCID https://orcid.org/0000-0002-5045-1198
Chun-Jiang WangCollege of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University Wuhan Hubei 430072 P. R. China xiuqindong@whu.edu.cn cjwang@whu.edu.cn.ORCID https://orcid.org/0000-0003-3629-6889
Wuhan University · CNTianjin University · CNHuazhong Agricultural University · CN

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Highly diastereo-/enantioselective assembly of 2,3-fused indolizine derivatives could be easily available through a cascade allylation/Friedel-Crafts type reaction enabled by a synergistic Cu/Ir catalysis. This designed protocol provides an unprecedented and facile route to enantioenriched indolizines bearing three stereogenic centers in moderate to high yields with excellent stereoselective control, which also featured broad substrate generality. Remarkably, four stereoisomers of the 2,3-fused indolizine products could be efficiently constructed in a predictable manner through the pairwise combination of copper and iridium catalysts. The synthetic utility of this method was readily elaborated by a gram-scale reaction, and synthetic transformations to other important chiral indolizine derivatives. Quantum mechanical explorations constructed a plausible synergetic catalytic cycle, revealed the origins of stereodivergence, and rationalized the protonation-stimulated stereoselective Friedel-Crafts type cyclization to form the indolizine products.

Identifiers

PMID37063803
PMCPMC10094240
OpenAlexW4324281386

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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.