Evidence map›Paper›PMID 37327329›Full record

ArticleScience advances2023

Enantioselective synthesis of α,α-diarylketones by sequential visible light photoactivation and phosphoric acid catalysis.

Hong-Fu Liu, Liang Long, Zhi-Qiang Zhu, Teng-Fei Wu, Yi-Rui Zhang, Han-Peng Pan, Ai-Jun Ma, Jin-Bao Peng, Yong-Heng Wang, Hao Gao and 1 more

Open access · goldAbstract read
In one paragraph

Article in Science advances, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
1.9field-weighted citation impact, top 15% 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

3 citing papers in PubMed, 13 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

11 authors at 2 institutions in 2 countries.

Hong-Fu LiuSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.ORCID 0009-0002-0667-069X
Liang LongInstitute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education of China (MOE), Jinan University, Guangzhou 510632, China.ORCID 0009-0006-1754-3054
Zhi-Qiang ZhuSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.
Teng-Fei WuSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.
Yi-Rui ZhangSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.
Han-Peng PanSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.
Ai-Jun MaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.ORCID 0000-0001-7757-0800
Jin-Bao PengSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.
Yong-Heng WangInstitute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education of China (MOE), Jinan University, Guangzhou 510632, China.
Hao GaoInstitute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education of China (MOE), Jinan University, Guangzhou 510632, China.ORCID 0000-0003-1178-0121
Xiang-Zhi ZhangSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.ORCID 0000-0003-0631-0758
Wuyi University · CNMinistry of Education · TH

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Chiral ketones and their derivatives are useful synthetic intermediates for the synthesis of biologically active natural products and medicinally relevant molecules. Nevertheless, general and broadly applicable methods for enantioenriched acyclic α,α-disubstituted ketones, especially α,α-diarylketones, remain largely underdeveloped, owing to the easy racemization. Here, we report a visible light photoactivation and phosphoric acid-catalyzed alkyne-carbonyl metathesis/transfer hydrogenation one-pot reaction using arylalkyne, benzoquinone, and Hantzsch ester for the expeditious synthesis of α,α-diarylketones with excellent yields and enantioselectivities. In the reaction, three chemical bonds, including C═O, C─C, and C─H, are formed, providing a de novo synthesis reaction for chiral α,α-diarylketones. Moreover, this protocol provides a convenient and practical method to synthesize or modify complex bioactive molecules, including efficient routes to florylpicoxamid and BRL-15572 analogs. Computational mechanistic studies revealed that C-H/π interactions, π-π interaction, and the substituents of Hantzsch ester all play crucial roles in the stereocontrol of the reaction.

Indexed as

EstersKetonesCatalysisPhosphoric AcidsPyridinesStereoisomerismEstersflorylpicoxamidKetonesphosphoric acidPhosphoric AcidsPyridines

Identifiers

PMID37327329
PMCPMC10275591
OpenAlexW4380986240

What OpenQuestion holds

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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.