Evidence map›Paper›PMID 36111677›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022

Brønsted Acid versus Phase-Transfer Catalysis in the Enantioselective Transannular Aminohalogenation of Enesultams.

Javier Luis-Barrera, Sandra Rodriguez, Uxue Uria, Efraim Reyes, Liher Prieto, Luisa Carrillo, Manuel Pedrón, Tomás Tejero, Pedro Merino, Jose L Vicario

Abstract read
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Asymmetric phase-transfer catalysis.Nature reviews. Chemistry · 2024
    Review
  2. 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.

Javier Luis-BarreraDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU) P.O. Box 644, 48080, Bilbao, Spain.
Sandra RodriguezDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU) P.O. Box 644, 48080, Bilbao, Spain.
Uxue UriaDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU) P.O. Box 644, 48080, Bilbao, Spain.ORCID http://orcid.org/0000-0003-0372-7005
Efraim ReyesDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU) P.O. Box 644, 48080, Bilbao, Spain.ORCID http://orcid.org/0000-0003-2038-9925
Liher PrietoDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU) P.O. Box 644, 48080, Bilbao, Spain.ORCID http://orcid.org/0000-0001-7965-7168
Luisa CarrilloDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU) P.O. Box 644, 48080, Bilbao, Spain.ORCID http://orcid.org/0000-0001-5208-6780
Manuel PedrónInstituto de Biocomputación y Fisica de Sistemas Complejos (BIFI), Universidad de Zaragoza, 50009, Zaragoza, Spain.ORCID http://orcid.org/0000-0003-4249-6748
Tomás TejeroInstituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-CSIC, 50009, Zaragoza, Spain.ORCID http://orcid.org/0000-0003-3433-6701
Pedro MerinoInstituto de Biocomputación y Fisica de Sistemas Complejos (BIFI), Universidad de Zaragoza, 50009, Zaragoza, Spain.ORCID http://orcid.org/0000-0002-2202-3460
Jose L VicarioDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU) P.O. Box 644, 48080, Bilbao, Spain.ORCID http://orcid.org/0000-0001-6557-1777

Funding

Eusko Jaurlaritza IT1558-22Eusko Jaurlaritza postdoctoral contract to J. L-B.Gobierno de Aragón Grupos 17R-34Gobierno de Aragón Predoctoral grant to M. P.Ministerio de Ciencia e Innovación FEDER PID2019-104090RB-100Ministerio de Ciencia e Innovación FEDER PID2020-118422GB-I00Ministerio de Educación, Cultura y Deporte FPU fellowship to S. R.
6 · The paper itself

Abstract

We have studied the enantioselective transannular aminohalogenation reaction of unsaturated medium-sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase-transfer catalysis. Under optimized conditions, a variety of bicyclic adducts can be obtained with good yields and high enantioselectivities. The mechanism of the reaction was also studied by using computational tools; we observed that the reaction involves the participation of a conformer of the nine-membered cyclic substrate with planar chirality in which the stereochemical outcome is controlled by the relative reactivity of the two pseudorotational enantiomers when interacting with the chiral catalyst.

Indexed as

AcidsCatalysisStereoisomerismAcidsasymmetric catalysiscomputational chemistryelectrophilic additionELFmedium-ring compoundstransannular reactions

Identifiers

PMID36111677
PMCPMC10053555

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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.