Evidence map›Paper›PMID 37830497›Full record

ArticleOrganic letters2023

Directing the Stereoselectivity of the Claisen Rearrangement to Form Cyclic Ketones with Full Substitution at the α-Positions.

Fatimat O Badmus, Raju S Thombal, Satish Chandra Philkhana, Joshua A Malone, Christian E Bailey, Estefania Armendariz-Gonzalez, Edward W Mureka, Cale M Locicero, Frank R Fronczek, Rendy Kartika

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Organic letters, 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
–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

1 citing paper in PubMed.

  1. Synthesis ofTetrahedron · 2025
    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.

Fatimat O BadmusDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Raju S ThombalDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Satish Chandra PhilkhanaDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Joshua A MaloneDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Christian E BaileyDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Estefania Armendariz-GonzalezDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Edward W MurekaDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Cale M LociceroDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
Frank R FronczekDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.ORCID 0000-0001-5544-2779
Rendy KartikaDepartment of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States.ORCID 0000-0002-2042-2812

Funding

New Synthetic Chemistries Enabled by Oxyallyl and 2-Aminoallyl CationsR01GM127649 · NIGMS · LOUISIANA STATE UNIV A&M COL BATON ROUGE · PI KARTIKA, RENDY GREGORY · 2018 to 2022
$1.4M
NIGMS NIH HHS R01 GM127649
6 · The paper itself

Abstract

We report an enantioselective synthesis of cyclic ketones with full substitutions at the α-positions in a highly diastereoselective manner. Our method is achieved by subjecting substrate motifs in 2-allyloxyenones to chiral organomagnesium reagents, which trigger the Claisen rearrangement upon direct 1,2-carbonyl addition. The observed diastereoselectivity of the allyl migration is proposed to originate from the intramolecular chelation of the magnesium alkoxide to the allyloxy moiety.

Identifiers

PMID37830497
PMCPMC10616857

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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.