Evidence map›Paper›PMID 36277630›Full record

ArticleChemical science2022

Decoded fingerprints of hyperresponsive, expanding product space: polyether cascade cyclizations as tools to elucidate supramolecular catalysis.

Hao Chen, Tian-Ren Li, Naomi Sakai, Celine Besnard, Laure Guénée, Marion Pupier, Jasmine Viger-Gravel, Konrad Tiefenbacher, Stefan Matile

Abstract read
In one paragraph

Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Anion-π catalysis on carbon allotropes.Beilstein journal of organic chemistry · 2023
    Review
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

9 authors.

Hao ChenNational Centre of Competence in Research (NCCR) Molecular Systems Engineering BPR 1095 Basel Switzerland.
Tian-Ren LiNational Centre of Competence in Research (NCCR) Molecular Systems Engineering BPR 1095 Basel Switzerland.
Naomi SakaiNational Centre of Competence in Research (NCCR) Molecular Systems Engineering BPR 1095 Basel Switzerland.ORCID https://orcid.org/0000-0002-9460-1944
Celine BesnardSchool of Chemistry and Biochemistry University of Geneva Geneva Switzerland stefan.matile@unige.ch https://www.unige.ch/sciences/chiorg/matile/ +41 22 379 6523.ORCID https://orcid.org/0000-0001-5699-9675
Laure GuénéeSchool of Chemistry and Biochemistry University of Geneva Geneva Switzerland stefan.matile@unige.ch https://www.unige.ch/sciences/chiorg/matile/ +41 22 379 6523.
Marion PupierSchool of Chemistry and Biochemistry University of Geneva Geneva Switzerland stefan.matile@unige.ch https://www.unige.ch/sciences/chiorg/matile/ +41 22 379 6523.
Jasmine Viger-GravelSchool of Chemistry and Biochemistry University of Geneva Geneva Switzerland stefan.matile@unige.ch https://www.unige.ch/sciences/chiorg/matile/ +41 22 379 6523.ORCID https://orcid.org/0000-0003-4627-7972
Konrad TiefenbacherNational Centre of Competence in Research (NCCR) Molecular Systems Engineering BPR 1095 Basel Switzerland.ORCID https://orcid.org/0000-0002-3351-6121
Stefan MatileNational Centre of Competence in Research (NCCR) Molecular Systems Engineering BPR 1095 Basel Switzerland.ORCID https://orcid.org/0000-0002-8537-8349

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Simple enough to be understood and complex enough to be revealing, cascade cyclizations of diepoxides are introduced as new tools to characterize supramolecular catalysis. Decoded product fingerprints are provided for a consistent set of substrate stereoisomers, and shown to report on chemo-, diastereo- and enantioselectivity, mechanism and even autocatalysis. Application of the new tool to representative supramolecular systems reveals, for instance, that pnictogen-bonding catalysis is not only best in breaking the Baldwin rules but also converts substrate diastereomers into completely different products. Within supramolecular capsules, new cyclic hemiacetals from House-Meinwald rearrangements are identified, and autocatalysis on anion-π catalysts is found to be independent of substrate stereochemistry. Decoded product fingerprints further support that the involved epoxide-opening polyether cascade cyclizations are directional, racemization-free, and interconnected, at least partially. The discovery of unique characteristics for all catalysts tested would not have been possible without decoded cascade cyclization fingerprints, thus validating the existence and significance of privileged platforms to elucidate supramolecular catalysis. Once decoded, cascade cyclization fingerprints are easily and broadly applicable, ready for use in the community.

Identifiers

PMID36277630
PMCPMC9473502

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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.