Evidence map›Paper›PMID 42599483›Full record

ArticleThe Journal of organic chemistry2026

Regiospecific Allenylation of Ketones with Propargyltrichlorosilane.

Noble Brako, Angela Coppola, Tristan Dales, Jada Hickerson, Turan Mienville, Ava Storey, Burjor Captain, Rajeev Prabhakar, Norito Takenaka

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

9 authors.

Noble BrakoDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida32901-6975, United States.ORCID 0009-0008-0406-7399
Angela CoppolaDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida32901-6975, United States.
Tristan DalesDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida32901-6975, United States.
Jada HickersonDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida32901-6975, United States.
Turan MienvilleDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida32901-6975, United States.
Ava StoreyDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida32901-6975, United States.
Burjor CaptainDepartment of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida33146-0431, United States.ORCID 0000-0002-7272-5655
Rajeev PrabhakarDepartment of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida33146-0431, United States.ORCID 0000-0003-1137-1272
Norito TakenakaDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida32901-6975, United States.ORCID 0000-0003-3542-1086

Funding

Enantioselective Catalytic Chlorosilane ReactionsR15GM139087 · NIGMS · FLORIDA INSTITUTE OF TECHNOLOGY · PI TAKENAKA, NORITO · 2020 to 2024
$869k
Acquisition of timsTOF Pro for Complex Lipidomic AnalysesS10OD030250 · OD · UNIVERSITY OF FLORIDA · PI BASSO, KARI B · 2022 to 2022
$658k
Acquisition of a Q Exactive HF Hybrid Quadrupole-OrbitrapS10OD021758 · OD · UNIVERSITY OF FLORIDA · PI BASSO, KARI B · 2017 to 2017
$600k
NIGMS NIH HHS R15 GM139087NIH HHS 2R15 GM139087-02NIH HHS S10 OD021758NIH HHS S10 OD021758-01A1NIH HHS S10 OD030250NIH HHS S10 OD030250-01A1
6 · The paper itself

Abstract

The inherent difficulty in eliciting regio-control over propargyl-allenyl isomerization of the corresponding metal/metalloid species has limited their utility as nucleophiles in organic synthesis. Consequently, synthetically versatile α-allenyl tertiary alcohols are generally synthesized in two steps from ketones (e.g., Crabbé homologation of propargylic alcohols) rather than by the direct addition of allenylation reagents to ketones. We have developed a regiospecific allenylation of ketones with isomerically pure propargyltrichlorosilane as an operationally simple, general method to prepare racemic monosubstituted α-allenyl tertiary alcohols. The method provided 29 α-allenyl tertiary alcohols in 8-99% isolated yields but it proved to be intolerant of ketones containing sterically large groups and enones.

Identifiers

PMID42599483
PMCPMC13476534

What OpenQuestion holds

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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.