Evidence map›Paper›PMID 34084440›Full record

ArticleChemical science2021

Nickel-catalyzed enantioselective vinylation of aryl 2-azaallyl anions.

Shengzu Duan, Guogang Deng, Yujin Zi, Xiaomei Wu, Xun Tian, Zhengfen Liu, Minyan Li, Hongbin Zhang, Xiaodong Yang, Patrick J Walsh

Open access · diamondAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical science, 2021. 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
1.4field-weighted citation impact, top 21% 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, 18 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

10 authors at 2 institutions in 4 countries.

Shengzu DuanKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Guogang DengKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Yujin ZiKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Xiaomei WuKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Xun TianKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Zhengfen LiuKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Minyan LiRoy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia PA USA pwalsh@sas.upenn.edu liminyan@sas.upenn.edu.
Hongbin ZhangKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-2516-2634
Xiaodong YangKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-8466-5418
Patrick J WalshRoy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia PA USA pwalsh@sas.upenn.edu liminyan@sas.upenn.edu.ORCID https://orcid.org/0000-0001-8392-4150
Yunnan University · CNCalifornia University of Pennsylvania · US

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A unique enantioselective nickel-catalyzed vinylation of 2-azaallyl anions is advanced for the first time. This method affords diverse vinyl aryl methyl amines with high enantioselectivities, which are frequently occurring scaffolds in natural products and medications. This C-H functionalization method can also be extended to the synthesis of enantioenriched 1,3-diamine derivatives by employing suitably elaborated vinyl bromides. Key to the success of this process is the identification of a Ni/chiraphos catalyst system and a less reducing 2-azaallyl anion, all of which favor an anionic vinylation route over a background radical reaction. A telescoped gram scale synthesis and a product derivatization study confirmed the scalability and synthetic potential of this method.

Identifiers

PMID34084440
PMCPMC8115067
OpenAlexW3142140780

What OpenQuestion holds

Textmetadata
LicenceCC BY
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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.