Evidence map›Paper›PMID 29608052›Full record

ReviewChemical reviews2018

Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

Yi Zhu, Jianlin Han, Jiandong Wang, Norio Shibata, Mikiko Sodeoka, Vadim A Soloshonok, Jaime A S Coelho, F Dean Toste

Abstract readReview
In one paragraph

Review in Chemical reviews, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 98 papers.

0numbers the graph read from it
0cells of the map it votes in
98citing 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

98 citing papers in PubMed.

  1. Article
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  5. Article
  6. Palladium-catalyzed asymmetric carbofluorination ofChemical communications (Cambridge, England) · 2026
    Article
  7. Article
  8. Article
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  10. Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. FluoBase: a fluorinated agents database.Journal of cheminformatics · 2025
    Article
  18. Synthesis ofJournal of the American Chemical Society · 2024
    Article
  19. Review
  20. Article

38 more citing papers are in PubMed but not listed here.

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.

Yi ZhuSchool of Chemistry and Chemical Engineering, State Key laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials , Nanjing University , 210093 Nanjing , China.
Jianlin HanSchool of Chemistry and Chemical Engineering, State Key laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials , Nanjing University , 210093 Nanjing , China.ORCID 0000-0002-3817-0764
Jiandong WangDepartment of Nanopharmaceutical Sciences & Department of Frontier Materials , Nagoya Institute of Technology , Gokiso, Showa-ku , Nagoya 466-8555 , Japan.
Norio ShibataDepartment of Nanopharmaceutical Sciences & Department of Frontier Materials , Nagoya Institute of Technology , Gokiso, Showa-ku , Nagoya 466-8555 , Japan.ORCID 0000-0002-3742-4064
Mikiko SodeokaSynthetic Organic Chemistry Laboratory , RIKEN, and RIKEN Center for Sustainable Resourse Science , 2-1 Hirosawa , Wako 351-0198 , Japan.ORCID 0000-0002-1344-364X
Vadim A SoloshonokDepartment of Organic Chemistry I, Faculty of Chemistry , University of the Basque Country UPV/EHU , 20018 San Sebastian , Spain.ORCID 0000-0003-0681-4526
Jaime A S CoelhoDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.
F Dean TosteDepartment of Chemistry , University of California , Berkeley , California 94720 , United States.ORCID 0000-0001-8018-2198

Funding

Methods for Selective Organic Synthesis based on Ionic CatalystsR35GM118190 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI F. Dean Toste · 2016 to 2026
$6.7M
NIGMS NIH HHS R35 GM118190
6 · The paper itself

Abstract

New methods for preparation of tailor-made fluorine-containing compounds are in extremely high demand in nearly every sector of chemical industry. The asymmetric construction of quaternary C-F stereogenic centers is the most synthetically challenging and, consequently, the least developed area of research. As a reflection of this apparent methodological deficit, pharmaceutical drugs featuring C-F stereogenic centers constitute less than 1% of all fluorine-containing medicines currently on the market or in clinical development. Here we provide a comprehensive review of current research activity in this area, including such general directions as asymmetric electrophilic fluorination via organocatalytic and transition-metal catalyzed reactions, asymmetric elaboration of fluorine-containing substrates via alkylations, Mannich, Michael, and aldol additions, cross-coupling reactions, and biocatalytic approaches.

Indexed as

AlkylationCarbonCatalysisChemistry Techniques, SyntheticCoordination ComplexesFluorineHalogenationMolecular StructurePharmaceutical PreparationsStereoisomerismTransition ElementsCarbonCoordination ComplexesFluorinePharmaceutical PreparationsTransition Elements

Identifiers

PMID29608052
PMCPMC6497456

What OpenQuestion holds

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Registered trials

None linked

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.