Evidence map›Paper›PMID 21830777›Full record

ArticleJournal of the American Chemical Society2011

Deacylative allylation: allylic alkylation via retro-Claisen activation.

Alexander J Grenning, Jon A Tunge

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.

0numbers the graph read from it
0cells of the map it votes in
11citing 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

11 citing papers in PubMed.

  1. Enantioconvergent Deacylative Functionalization toward α-Quaternary Nitriles.Angewandte Chemie (International ed. in English) · 2025
    Article
  2. Highly Stereospecific Cyclizations of Homoallylic Silanols.The Journal of organic chemistry · 2022
    Article
  3. Dihydroquinazolinones as adaptative C(spNature communications · 2022
    Article
  4. Article
  5. Review
  6. Article
  7. Article
  8. Article
  9. Synthesis of diarylmethylaminesChemical science · 2014
    Article
  10. Article
  11. Development of asymmetric deacylative allylation.The Journal of organic chemistry · 2013
    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

2 authors.

Alexander J GrenningDepartment of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7528, USA.
Jon A Tunge

Funding

Synthetic Methods Involving Decarboxylative CouplingR01GM079644 · NIGMS · UNIVERSITY OF KANSAS LAWRENCE · PI TUNGE, JON A · 2007 to 2011
$1.3M
NIGMS NIH HHS 1R01GM079644NIGMS NIH HHS R01 GM079644
6 · The paper itself

Abstract

A new method for allylic alkylation of a variety of relatively nonstabilized carbon nucleophiles is described herein. In this process of "deacylative allylation", the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in situ retro-Claisen activation to generate an allylic acetate and a carbanion. In the presence of palladium, these reactive intermediates undergo catalytic coupling to form a new C-C bond. In comparison to unimolecular decarboxylative allylation, a commonly utilized method for allylation of carbon anions, deacylative allylation is an intermolecular process. Moreover, deacylative allylation allows the direct coupling of readily available allylic alcohols. Lastly, the full utility of deacylative allylation is demonstrated by the rapid construction of a variety 1,6-heptadienes via 3-component couplings.

Indexed as

AcetatesAlkylationAllyl CompoundsKetonesPropanolsStereoisomerismAcetatesallyl acetateallyl alcoholAllyl CompoundsKetonesPropanols

Identifiers

PMID21830777
PMCPMC3179378

What OpenQuestion holds

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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.