Evidence map›Paper›PMID 35976157›Full record

ArticleJournal of the American Chemical Society2022

Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.

Jin Zhu, Yidong Wang, Aaron D Charlack, Yi-Ming Wang

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing 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

9 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Accessing Z-Enynes via Cobalt-Catalyzed Propargylic Dehydrogenation.Angewandte Chemie (International ed. in English) · 2024
    Article
  6. Article
  7. Article
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  9. 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

4 authors.

Jin ZhuDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania15260, United States.
Yidong WangDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania15260, United States.ORCID 0000-0001-9560-3186
Aaron D CharlackDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania15260, United States.
Yi-Ming WangDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania15260, United States.ORCID 0000-0001-6414-0908

Funding

New Strategies and Reactions for the α-C–H Functionalization and Hydrofunctionalization of Carbon–Carbon Multiple BondsR35GM142945 · NIGMS · UNIVERSITY OF PITTSBURGH AT PITTSBURGH · PI WANG, YIMING · 2021 to 2025
$1.9M
NIGMS NIH HHS R35 GM142945
6 · The paper itself

Abstract

An iridium-catalyzed stereoselective coupling of allylic ethers and alkynes to generate 3,4-substituted 1,5-enynes is reported. Under optimized conditions, the coupling products are formed with excellent regio-, diastereo-, and enantioselectivities, and the protocol is functional group tolerant. Moreover, we report conditions that allow the reaction to proceed with complete reversal of diastereoselectivity. Mechanistic studies are consistent with an unprecedented dual role for the iridium catalyst, enabling the propargylic deprotonation of the alkyne through π-coordination, as well as the generation of a π-allyl species from the allylic ether starting material.

Indexed as

Allyl CompoundsIridiumAlkynesCatalysisEthersStereoisomerismAlkynesAllyl CompoundsEthersIridium

Identifiers

PMID35976157
PMCPMC9437123

What OpenQuestion holds

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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 OpenQuestion graph.