Evidence map›Paper›PMID 31050428›Full record

ArticleThe Journal of organic chemistry2019

Mechanistic Perspectives in the Regioselective Indole Addition to Unsymmetrical Silyloxyallyl Cations.

Caitlin G Bresnahan, Kiara A Taylor-Edinbyrd, Alexander H Cleveland, Joshua A Malone, Nitin S Dange, Anne Milet, Revati Kumar, Rendy Kartika

Open access · greenAbstract read
In one paragraph

Article in The Journal of organic chemistry, 2019. 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
0.4field-weighted citation impact, top 44% 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

2 citing papers in PubMed, 5 citations in OpenAlex.

  1. HFIP-Induced Formation ofThe Journal of organic chemistry · 2026
    Article
  2. 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

8 authors at 2 institutions in 2 countries.

Caitlin G BresnahanDepartment of Chemistry , Louisiana State University , 232 Choppin Hall , Baton Rouge , Louisiana 70803 , United States.
Kiara A Taylor-EdinbyrdDepartment of Chemistry , Louisiana State University , 232 Choppin Hall , Baton Rouge , Louisiana 70803 , United States.
Alexander H ClevelandDepartment 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.
Nitin S DangeDepartment of Chemistry , Louisiana State University , 232 Choppin Hall , Baton Rouge , Louisiana 70803 , United States.ORCID 0000-0003-0356-2511
Anne MiletDépartement de Chimie Moléculaire, Université Grenoble Alpes, CNRS, UMR 5250 , F-38000 Grenoble , France.ORCID 0000-0002-1480-4451
Revati KumarDepartment of Chemistry , Louisiana State University , 232 Choppin Hall , Baton Rouge , Louisiana 70803 , United States.ORCID 0000-0002-3272-8720
Rendy KartikaDepartment of Chemistry , Louisiana State University , 232 Choppin Hall , Baton Rouge , Louisiana 70803 , United States.ORCID 0000-0002-2042-2812
Louisiana State University · USCentre National de la Recherche Scientifique · FR

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

Our investigations on the reaction mechanism to account for regioselectivity on the addition of indoles to unsymmetrical silyloxyallyl cations are reported. Using both experimental and computational methods, we confirmed the significance of steric effects from the silyl ether group toward directing the inward approach of indoles, leading to nucleophilic attack at the less substituted electrophilic α'-carbon. The role of residual water toward accelerating the rate of reaction is established through stabilization of the participating silyloxyallyl cation.

Indexed as

CationsEpoxy CompoundsIndolesMolecular StructureOrganosilicon CompoundsStereoisomerismCationsEpoxy CompoundsindoleIndolesOrganosilicon Compounds

Identifiers

PMID31050428
PMCPMC7055495
OpenAlexW2943124716

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.