Evidence map›Paper›PMID 33476142›Full record

ArticleThe Journal of organic chemistry2021

Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements.

Ehsan Fereyduni, Ouidad Lahtigui, Jacob N Sanders, Breanna M Tomiczek, Michael D Mannchen, Roland A Yu, K N Houk, Alexander J Grenning

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
  2. Article
  3. Vicinal stereocentersChemical science · 2023
    Article
  4. 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.

Ehsan FereyduniDepartment of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611, United States.
Ouidad LahtiguiDepartment of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611, United States.
Jacob N SandersDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.ORCID 0000-0002-2196-4234
Breanna M TomiczekDepartment of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611, United States.
Michael D MannchenDepartment of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611, United States.
Roland A YuDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.ORCID 0000-0002-8387-5261
Alexander J GrenningDepartment of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611, United States.ORCID 0000-0002-8182-9464

Funding

New opportunities for the Cope rearrangement: methods, modular synthesis, and applications in drug discoveryR35GM137893 · NIGMS · UNIVERSITY OF MINNESOTA · PI GRENNING, ALEXANDER JAMES · 2020 to 2024
$1.8M
Acquisition of a Q Exactive HF Hybrid Quadrupole-OrbitrapS10OD021758 · OD · UNIVERSITY OF FLORIDA · PI BASSO, KARI B · 2017 to 2017
$600k
Development of New Methods for Computational Enzyme DesignF32GM122218 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI SANDERS, JACOB NATHAN · 2017 to 2019
$176k
NIGMS NIH HHS F32 GM122218NIGMS NIH HHS R35 GM137893NIH HHS S10 OD021758
6 · The paper itself

Abstract

Systematic evaluation of 1,5-dienes bearing 3,3-electron-withdrawing groups and 4-methylation results in the discovery of a Cope rearrangement for Meldrum's acid-containing substrates that have unexpectedly favorable kinetic and thermodynamic profiles. The protocol is quite general due to a concise and convergent synthesis from abundant starting materials. Furthermore, products with an embedded Meldrum's acid moiety are prepared, which, in turn, can yield complex amides under neutral conditions. We have now expanded the scope of the reductive Cope rearrangement, which, via chemoselective reduction, can promote thermodynamically unfavorable [3,3] sigmatropic rearrangements of 3,3-dicyano-1,5-dienes to form reduced Cope rearrangement products. The Cope rearrangement is found to be stereospecific and can yield enantioenriched building blocks when chiral, nonracemic 1,3-disubstituted allylic electrophiles are utilized. We expand further the use of Cope rearrangements for the synthesis of highly valuable building blocks for complex- and drug-like molecular synthesis.

Indexed as

PolyenesKineticsThermodynamicsPolyenes

Identifiers

PMID33476142
PMCPMC8195263

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.