Evidence map›Paper›PMID 38664372›Full record

ArticleNature communications2024

Iron-catalyzed stereoselective C-H alkylation for simultaneous construction of C-N axial and C-central chirality.

Zi-Jing Zhang, Nicolas Jacob, Shilpa Bhatia, Philipp Boos, Xinran Chen, Joshua C DeMuth, Antonis M Messinis, Becky Bongsuiru Jei, João C A Oliveira, Aleksa Radović and 3 more

Open access · goldAbstract read
In one paragraph

Article in Nature communications, 2024. 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
8.0field-weighted citation impact, top 2% of its field
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, 32 citations in OpenAlex.

  1. Article
  2. Installing Axial Chirality by Atroposelective C(spJournal of the American Chemical Society · 2026
    Article
  3. Article
  4. Article
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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

13 authors at 4 institutions in 5 countries.

Zi-Jing ZhangInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany.
Nicolas JacobLaboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg/Université de Haute-Alsace, ECPM, 67087, Strasbourg, France.
Shilpa BhatiaDepartment of Chemistry, University of Rochester, Rochester, NY, 14627, USA.
Philipp BoosInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany.ORCID http://orcid.org/0009-0004-7864-1833
Xinran ChenInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany.
Joshua C DeMuthDepartment of Chemistry, University of Rochester, Rochester, NY, 14627, USA.
Antonis M MessinisInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany.ORCID http://orcid.org/0000-0002-6168-355X
Becky Bongsuiru JeiInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany.
João C A OliveiraInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany.ORCID http://orcid.org/0000-0002-2990-0315
Aleksa RadovićDepartment of Chemistry, University of Rochester, Rochester, NY, 14627, USA.
Michael L NeidigInorganic Chemistry Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, OX1 3QR, UK. michael.neidig@chem.ox.ac.uk.ORCID http://orcid.org/0000-0002-2300-3867
Joanna Wencel-DelordLaboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg/Université de Haute-Alsace, ECPM, 67087, Strasbourg, France. wenceldelord@unistra.fr.ORCID http://orcid.org/0000-0002-7094-5443
Lutz AckermannInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany. Lutz.Ackermann@chemie.uni-goettingen.de.ORCID http://orcid.org/0000-0001-7034-8772
University of Göttingen · DEUniversity of Rochester · USCentre National de la Recherche Scientifique · FRUniversity of Oxford · GB

Funding

Deutsche Forschungsgemeinschaft (German Research Foundation) Gottfried Wilhelm Leibniz awardDeutsche Forschungsgemeinschaft (German Research Foundation) SPP1807National Science Foundation (NSF) CHE-1954480
6 · The paper itself

Abstract

The assembly of chiral molecules with multiple stereogenic elements is challenging, and, despite of indisputable advances, largely limited to toxic, cost-intensive and precious metal catalysts. In sharp contrast, we herein disclose a versatile C-H alkylation using a non-toxic, low-cost iron catalyst for the synthesis of substituted indoles with two chiral elements. The key for achieving excellent diastereo- and enantioselectivity was substitution on a chiral N-heterocyclic carbene ligand providing steric hindrance and extra represented by noncovalent interaction for the concomitant generation of C-N axial chirality and C-stereogenic center. Experimental and computational mechanistic studies have unraveled the origin of the catalytic efficacy and stereoselectivity.

Identifiers

PMID38664372
PMCPMC11045758
OpenAlexW4395450284

What OpenQuestion holds

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LicenceCC BY
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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.