Evidence map›Paper›PMID 37129272›Full record

ArticleChirality2023

Enantioseparation and racemization of 3-fluorooxindoles.

Andi Yuan, Sarah E Steber, Dea Xhili, Eryn Nelson, Christian Wolf

Open access · bronzeAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chirality, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
0.1field-weighted citation impact, top 56% 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

1 citing paper in PubMed, 1 citations in OpenAlex.

  1. 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 at 1 institution in 1 country.

Andi YuanDepartment of Chemistry, Georgetown University, Washington, DC, USA.
Sarah E SteberDepartment of Chemistry, Georgetown University, Washington, DC, USA.
Dea XhiliDepartment of Chemistry, Georgetown University, Washington, DC, USA.
Eryn NelsonDepartment of Chemistry, Georgetown University, Washington, DC, USA.
Christian WolfDepartment of Chemistry, Georgetown University, Washington, DC, USA.ORCID https://orcid.org/0000-0002-4447-3753
Georgetown University · US

Funding

Synthesis of Chiral Organofluorines via Catalytic Asymmetric C-C Bond Formation wR15GM106260 · NIGMS · GEORGETOWN UNIVERSITY · PI Christian Wolf · 2013 to 2026
$2.2M
NIGMS NIH HHS R15 GM106260
6 · The paper itself

Abstract

Fluorinated oxindoles are frequently used building blocks in asymmetric synthesis and represent an important scaffold found in a variety of biologically relevant compounds. While it is understood that incorporation of fluorine atoms into organic molecules can improve their pharmacological properties, the impact on the configurational stability of chiral organofluorines is still underexplored. In this study, semipreparative HPLC enantioseparations of five oxindoles were carried out, and the resulting enantiomerically enriched solutions were used to investigate base promoted racemization kinetics at room temperature. It was found that incorporation of fluorine at the chiral center increases the configurational stability, while substitutions on the aromatic ring and at the lactam moiety also have significant effects on the rate of racemization, which generally follows reversible first-order reaction kinetics.

Indexed as

configurational stabilityenantioconversionenantioseparationfluoride effecthigh performance liquid chromatographyoxindoles

Identifiers

PMID37129272
PMCPMC10516598
OpenAlexW4367668735

What OpenQuestion holds

Textmetadata
LicenceTDM
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 OpenQuestion graph.