Evidence map›Paper›PMID 39624656›Full record

ArticleBeilstein journal of organic chemistry2024

Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline

Noble Brako, Sreerag Moorkkannur Narayanan, Amber Burns, Layla Auter, Valentino Cesiliano, Rajeev Prabhakar, Norito Takenaka

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Beilstein journal of organic chemistry, 2024. 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. New advances in asymmetric organocatalysis II.Beilstein journal of organic chemistry · 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

7 authors.

Noble BrakoDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA.ORCID https://orcid.org/0009-0008-0406-7399
Sreerag Moorkkannur NarayananDepartment of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33146-0431, USA.ORCID https://orcid.org/0000-0001-5075-6947
Amber BurnsDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA.ORCID https://orcid.org/0009-0007-4752-4169
Layla AuterDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA.ORCID https://orcid.org/0009-0000-3996-258X
Valentino CesilianoDepartment of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33146-0431, USA.ORCID https://orcid.org/0009-0005-1076-3313
Rajeev PrabhakarDepartment of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33146-0431, USA.ORCID https://orcid.org/0000-0003-1137-1272
Norito TakenakaDepartment of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA.ORCID https://orcid.org/0000-0003-3542-1086

Funding

Enantioselective Catalytic Chlorosilane ReactionsR15GM139087 · NIGMS · FLORIDA INSTITUTE OF TECHNOLOGY · PI TAKENAKA, NORITO · 2020 to 2024
$869k
NIGMS NIH HHS R15 GM139087
6 · The paper itself

Abstract

Distilled propargyltrichlorosilane with >99% isomeric purity was prepared for the first time, and its asymmetric catalytic regiospecific addition reaction to aldehydes was developed through a systematic catalyst structure-reactivity and selectivity relationship study. The observed catalyst structure-enantioselectivity relationship of the present allenylation reaction was found exactly opposite to that of the analogous allylation reaction. The method provided eleven α-allenic alcohols in 22-99% yield with 61:39-92:8 enantiomeric ratios. Furthermore, possible mechanisms of propargyl-allenyl isomerization of propargyltrichlorosilane were computationally investigated.

Indexed as

computational chemistryLewis base catalysisorganocatalysispropargyltrichlorosilaneα-allenic alcohol

Identifiers

PMID39624656
PMCPMC11610484

What Socratic holds

Textmetadata
LicenceCC BY
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 Socratic graph.