Evidence map›Paper›PMID 36082052›Full record

ArticleACS catalysis2022

Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes.

Kieran Nicholson, Yuxuan Peng, Natalia Llopis, Dominic R Willcox, Gary S Nichol, Thomas Langer, Alejandro Baeza, Stephen P Thomas

Abstract read
In one paragraph

Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing 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

7 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Formally Stereoretentive SJournal of the American Chemical Society · 2025
    Article
  5. Recent Advances in Asymmetric Catalysis Using p-Block Elements.Angewandte Chemie (International ed. in English) · 2024
    Review
  6. Group 13 exchange and transborylation in catalysis.Beilstein journal of organic chemistry · 2023
    Review
  7. Selective CspSynthesis · 2022
    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.

Kieran NicholsonEaStCHEM School of Chemistry, The University of Edinburgh, Joseph Black Building, Edinburgh EH9 3FJ, United Kingdom.
Yuxuan PengEaStCHEM School of Chemistry, The University of Edinburgh, Joseph Black Building, Edinburgh EH9 3FJ, United Kingdom.
Natalia LlopisEaStCHEM School of Chemistry, The University of Edinburgh, Joseph Black Building, Edinburgh EH9 3FJ, United Kingdom.
Dominic R WillcoxEaStCHEM School of Chemistry, The University of Edinburgh, Joseph Black Building, Edinburgh EH9 3FJ, United Kingdom.
Gary S NicholEaStCHEM School of Chemistry, The University of Edinburgh, Joseph Black Building, Edinburgh EH9 3FJ, United Kingdom.
Thomas LangerPharmaceutical Technology & Development, Chemical Development U.K., AstraZeneca, Silk Road, Macclesfield SK10 2NA, United Kingdom.
Alejandro BaezaInstituto de Síntesis Orgánica and Dpto. de Química Orgánica, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain.ORCID https://orcid.org/0000-0002-6230-1162
Stephen P ThomasEaStCHEM School of Chemistry, The University of Edinburgh, Joseph Black Building, Edinburgh EH9 3FJ, United Kingdom.ORCID https://orcid.org/0000-0001-8614-2947

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The diastereo- and enantioselective allylation of ketones remains a synthetic challenge, with transition metal catalysis offering the most applied methods. Here, a boron-catalyzed allylation of ketones with allenes is presented. Excellent yield, regioselectivity, and diastereoselectivity were found across functionalized substrates. The reaction was further developed to accommodate an enantioenriched boron catalyst and thus gave asymmetric ketone allylation in good yield, diastereoselectivity, and enantioselectivity. Mechanistic studies supported a hydroboration-allylation-transborylation pathway.

Identifiers

PMID36082052
PMCPMC9442582

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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.