Evidence map›Paper›PMID 31296850›Full record

ArticleNature communications2019

Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination.

He-Yuan Bai, Fu-Xin Tan, Tuan-Qing Liu, Guo-Dong Zhu, Jin-Miao Tian, Tong-Mei Ding, Zhi-Min Chen, Shu-Yu Zhang

Open access · goldAbstract read
In one paragraph

Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.

0numbers the graph read from it
0cells of the map it votes in
19citing papers in PubMed
6.2field-weighted citation impact, top 2% 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

19 citing papers in PubMed, 112 citations in OpenAlex.

  1. Article
  2. Recent advances in organocatalytic atroposelective reactions.Beilstein journal of organic chemistry · 2025
    Review
  3. Atroposelective catalysis.Nature reviews. Chemistry · 2024
    Review
  4. Review
  5. Article
  6. Article
  7. Article
  8. Article
  9. Article
  10. Review
  11. Review
  12. Article
  13. Review
  14. Asymmetric Synthesis of Axially Chiral C-N Atropisomers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022
    Review
  15. Article
  16. Enantioselective Aromatic Amination?Chemistry (Weinheim an der Bergstrasse, Germany) · 2021
    Article
  17. Review
  18. Article
  19. 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

8 authors at 1 institution in 1 country.

He-Yuan BaiShanghai Key Laboratory for Molecular Engineer of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.ORCID http://orcid.org/0000-0002-8986-6913
Fu-Xin TanShanghai Key Laboratory for Molecular Engineer of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.
Tuan-Qing LiuShanghai Key Laboratory for Molecular Engineer of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.
Guo-Dong ZhuShanghai Key Laboratory for Molecular Engineer of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.
Jin-Miao TianShanghai Key Laboratory for Molecular Engineer of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.
Tong-Mei DingShanghai Key Laboratory for Molecular Engineer of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.
Zhi-Min ChenShanghai Key Laboratory for Molecular Engineer of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.
Shu-Yu ZhangShanghai Key Laboratory for Molecular Engineer of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China. zhangsy16@sjtu.edu.cn.ORCID http://orcid.org/0000-0002-1811-4159
Shanghai Jiao Tong University · CN

Funding

National Natural Science Foundation of China (National Science Foundation of China) 21672145National Natural Science Foundation of China (National Science Foundation of China) 21702136Natural Science Foundation of Shanghai (Natural Science Foundation of Shanghai Municipality) 17JC1403700Shanghai Education Development Foundation (SHEDF) 16SG10
6 · The paper itself

Abstract

Nonbiaryl N-C atropisomer is an important structural scaffold, which is present in natural products, medicines and chiral ligands. However the direct enantioselective C-H amination to access optically pure N-C atropisomer is still difficult and rare. Here we report a π-π interaction and dual H-bond concerted control strategy to develop the chiral phosphoric acids (CPAs) catalyzed direct intermolecular enantioselective C-H amination of N-aryl-2-naphthylamines with azodicarboxylates as amino sources for the construction of atroposelective naphthalene-1,2-diamines. This type of N-C atropisomers is stabilized by intramolecular hydrogen bond and the method features a broad range of substrates, high yields and ee values, providing a strategy to chirality transfer via the modification of N-C atropisomers.

Identifiers

PMID31296850
PMCPMC6624262
OpenAlexW2957329010

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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.