Evidence map›Paper›PMID 37127757›Full record

ArticleNature chemistry2023

Catalytic enantioselective nucleophilic desymmetrization of phosphonate esters.

Michele Formica, Tatiana Rogova, Heyao Shi, Naoto Sahara, Branislav Ferko, Alistair J M Farley, Kirsten E Christensen, Fernanda Duarte, Ken Yamazaki, Darren J Dixon

Abstract read
In one paragraph

Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.

0numbers the graph read from it
0cells of the map it votes in
24citing 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

24 citing papers in PubMed.

  1. Kinetically Stable Boron-Heteroatom Bonds.Angewandte Chemie (International ed. in English) · 2026
    Article
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  11. Review
  12. Article
  13. Article
  14. Catalysis of an SNature · 2024
    Article
  15. Article
  16. Article
  17. Review
  18. Article
  19. Article
  20. 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

10 authors.

Michele FormicaChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.
Tatiana RogovaChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.ORCID http://orcid.org/0000-0001-7395-863X
Heyao ShiChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.
Naoto SaharaChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.
Branislav FerkoChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.
Alistair J M FarleyChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.ORCID http://orcid.org/0000-0001-5578-6790
Kirsten E ChristensenChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.ORCID http://orcid.org/0000-0003-1683-2066
Fernanda DuarteChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.ORCID http://orcid.org/0000-0002-6062-8209
Ken YamazakiDivision of Applied Chemistry, Okayama University, Okayama, Japan. k-yamazaki@okayama-u.ac.jp.ORCID http://orcid.org/0000-0002-2039-4321
Darren J DixonChemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK. darren.dixon@chem.ox.ac.uk.ORCID http://orcid.org/0000-0003-2456-5236

Funding

Canadian Network for Research and Innovation in Machining Technology, Natural Sciences and Engineering Research Council of Canada (NSERC Canadian Network for Research and Innovation in Machining Technology) PGSD3-532666-2019EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 Marie Skłodowska-Curie Actions (H2020 Excellent Science - Marie Skłodowska-Curie Actions) 10133408RCUK | Engineering and Physical Sciences Research Council (EPSRC) EP/L015838/1
6 · The paper itself

Abstract

Molecules that contain a stereogenic phosphorus atom are crucial to medicine, agrochemistry and catalysis. While methods are available for the selective construction of various chiral organophosphorus compounds, catalytic enantioselective approaches for their synthesis are far less common. Given the vastness of possible substituent combinations around a phosphorus atom, protocols for their preparation should also be divergent, providing facile access not only to one but to many classes of phosphorus compounds. Here we introduce a catalytic and enantioselective strategy for the preparation of an enantioenriched phosphorus(V) centre that can be diversified enantiospecifically to a wide range of biologically relevant phosphorus(V) compounds. The process, which involves an enantioselective nucleophilic substitution catalysed by a superbasic bifunctional iminophosphorane catalyst, can accommodate a wide range of carbon substituents at phosphorus. The resulting stable, yet versatile, synthetic intermediates can be combined with a multitude of medicinally relevant O-, N- and S-based nucleophiles.

Identifiers

PMID37127757
PMCPMC10159838

What Socratic holds

Textmetadata
LicenceCC BY
Read underepoch 390

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 Socratic graph.