Evidence map›Paper›PMID 33761252›Full record

ArticleJournal of the American Chemical Society2021

CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.

Sheng Feng, Stephen L Buchwald

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

0numbers the graph read from it
0cells of the map it votes in
10citing 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

10 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Copper-Catalyzed Diastereo-, Enantio-, and (Journal of the American Chemical Society · 2024
    Article
  6. Stereoselective Copper-Catalyzed Olefination of Imines.Angewandte Chemie (International ed. in English) · 2024
    Article
  7. Synthetic Advantages of Defluorinative C-F Bond Functionalization.Angewandte Chemie (International ed. in English) · 2023
    Review
  8. Article
  9. Article
  10. Review
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.

Sheng FengDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0001-8781-9681
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-3875-4775

Funding

Metal-Catalyzed Methods for Organic SynthesisR35GM122483 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI STEPHEN L BUCHWALD · 2017 to 2026
$11.4M
LATE TRANSITION METAL CATALYSTS FOR ORGANIC SYNTHESISR01GM058160 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1998 to 2016
$9.0M
NIGMS NIH HHS R01 GM058160NIGMS NIH HHS R35 GM122483
6 · The paper itself

Abstract

We report a method to prepare α-chiral carboxylic acid derivatives, including those bearing all-carbon quaternary centers, through an enantioselective CuH-catalyzed hydrocarboxylation of allenes with a commercially available fluoroformate. A broad range of heterocycles and functional groups on the allenes were tolerated in this protocol, giving enantioenriched α-quaternary and tertiary carboxylic acid derivatives in good yields with exclusive branched regioselectivity. The synthetic utility of this approach was further demonstrated by derivatization of the products to afford biologically important compounds, including the antiplatelet drug indobufen.

Indexed as

Carboxylic AcidsCatalysisCopperHydrocarbonsStereoisomerismCarboxylic AcidsCopperHydrocarbons

Identifiers

PMID33761252
PMCPMC8058699

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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.