Evidence map›Paper›PMID 29426851›Full record

ArticleNature communications2018

Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.

Changgui Zhao, Donghui Guo, Kristin Munkerup, Kuo-Wei Huang, Fangyi Li, Jian Wang

Abstract read
In one paragraph

Article in Nature communications, 2018. 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
–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

19 citing papers in PubMed.

  1. Review
  2. Review
  3. Article
  4. Article
  5. Article
  6. Article
  7. Article
  8. Review
  9. Review
  10. Oxidative N-Heterocyclic Carbene Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023
    Review
  11. A Review on Generation and Reactivity of theMolecules (Basel, Switzerland) · 2022
    Review
  12. Article
  13. Article
  14. Review
  15. Article
  16. Organocatalytic Name Reactions Enabled by NHCs.Materials (Basel, Switzerland) · 2020
    Review
  17. Construction of Dihydropyrido[2,3-The Journal of organic chemistry · 2020
    Article
  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

6 authors.

Changgui ZhaoSchool of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing, 100084, Beijing, China.
Donghui GuoSchool of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing, 100084, Beijing, China.
Kristin MunkerupDivision of Chemical and Life Sciences & Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal, 23955-6900, Saudi Arabia.ORCID http://orcid.org/0000-0001-7097-8133
Kuo-Wei HuangDivision of Chemical and Life Sciences & Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal, 23955-6900, Saudi Arabia.ORCID http://orcid.org/0000-0003-1900-2658
Fangyi LiSchool of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing, 100084, Beijing, China.
Jian WangSchool of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing, 100084, Beijing, China. wangjian2012@tsinghua.edu.cn.ORCID http://orcid.org/0000-0003-1884-4546

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a catalytic C-C bond formation occurs, providing axially chiral α-pyrone-aryls in moderate to good yields and with high enantioselectivities. Control experiments indicated that alkynyl acyl azoliums, acting as active intermediates, are employed to atroposelectively assemble chiral biaryls and such a methodology may be creatively applied to other useful NHC-catalyzed asymmetric transformations.

Identifiers

PMID29426851
PMCPMC5807440

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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.