Evidence map›Paper›PMID 41105738›Full record

ArticleThe Journal of organic chemistry2025

The Development of Stereoselective Substrate and Reagent-Controlled Lithiation-Borylation Chemistry.

Yannick Linne, Maike Birkner, Daniel Lücke, Jan Flormann, Kjeld Gerdes, Giada Tedesco, Gaia Stojanovic, Tom Jentsch, Birk Jäger, Kevin Bajerke and 2 more

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2025. 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

12 authors.

Yannick LinneInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.
Maike BirknerInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.
Daniel LückeInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.ORCID 0000-0001-5993-8261
Jan FlormannInstitute of Physical Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Callinstraße 3A, Hannover 30167, Germany.ORCID 0000-0002-1310-1420
Kjeld GerdesInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.
Giada TedescoInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.
Gaia StojanovicInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.
Tom JentschInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.
Birk JägerInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.
Kevin BajerkeInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.
Jörg August BeckerInstitute of Physical Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Callinstraße 3A, Hannover 30167, Germany.
Markus KalesseInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, Hannover 30167, Germany.ORCID 0000-0003-4858-3957

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Allylic alcohols are a privileged motif in polyketide-based natural product synthesis, and new methods that access them in a stereoselective fashion are highly sought after. Toward this goal, we found that the use of chiral polyketide fragments allows for performing the Hoppe-Matteson-Aggarwal rearrangement in the absence of sparteine with high yields and diastereoselectivities, rendering this protocol a highly valuable alternative to existing methods. Various stereodyads and -triads bearing different protecting and directing groups were investigated to determine their substrate induction. The mostly strong inherent induction was attributed to either steric or a combination of steric and electronic effects. The stereochemical outcome could be explained by (DFT-based) conformational analysis and a Felkin-like model, allowing guidance flowcharts to be created for the substrate- and reagent-controlled lithiation-borylation chemistry.

Identifiers

PMID41105738
PMCPMC12584137

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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.