Evidence map›Paper›PMID 40360493›Full record

ArticleNature communications2025

Desymmetric esterification catalysed by bifunctional chiral N-heterocyclic carbenes provides access to inherently chiral calix[4]arenes.

Vojtěch Dočekal, Ladislav Lóška, Adam Kurčina, Ivana Císařová, Jan Veselý

Abstract read
In one paragraph

Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing 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

8 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Review
  7. Enantioselective Desymmetrization by Chiral Bifunctional H-Bonding Organocatalysts.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Review
  8. 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

5 authors.

Vojtěch DočekalDepartment of Organic Chemistry, Faculty of Science, Charles University, Prague, Czech Republic. vojtech.docekal@natur.cuni.cz.ORCID http://orcid.org/0000-0003-3957-7977
Ladislav LóškaDepartment of Organic Chemistry, Faculty of Science, Charles University, Prague, Czech Republic.
Adam KurčinaDepartment of Organic Chemistry, Faculty of Science, Charles University, Prague, Czech Republic.
Ivana CísařováDepartment of Inorganic Chemistry, Faculty of Science, Charles University, Prague, Czech Republic.ORCID http://orcid.org/0000-0002-9612-9831
Jan VeselýDepartment of Organic Chemistry, Faculty of Science, Charles University, Prague, Czech Republic. jan.vesely@natur.cuni.cz.ORCID http://orcid.org/0000-0001-5198-8950

Funding

Přírodovědecká Fakulta, Univerzita Karlova (Faculty of Science, Charles University) UNCE/24/SCI/010
6 · The paper itself

Abstract

Calix[4]arenes display inherent chirality, with broad applications in synthetic and medicinal chemistry and in materials sciences. However, their use is hindered by their limited synthetic accessibility, primarily due to the lack of enantioselective methods for preparing chiral calix[4]arenes with an ABCC substitution pattern. Here, we address this challenge by presenting a simple, efficient, and metal-free protocol for organocatalytic desymmetrisation of prochiral diformylcalix[4]arenes. Through this highly effective and sustainable approach, we synthesize structurally unique products in gram-scale reactions. Accordingly, this method facilitates extensive post-functionalisations of the carbonyl groups, including for organocatalyst development. Furthermore, our experimental mechanistic studies demonstrate that desymmetrisation determines enantiocontrol in esterification reactions catalysed by N-heterocyclic carbenes. These findings underscore the broad potential of this method for providing versatile access to inherently chiral calix[4]arenes with an ABCC substitution pattern while offering a valuable platform for asymmetric molecular recognition and catalysis.

Identifiers

PMID40360493
PMCPMC12075856

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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.