Cited by 53Catalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsAsymmetric Synthesis and Catalysis

Modular, stereocontrolled C β –H/C α –C activation of alkyl carboxylic acids

Open access
Shang, Ming, Feu, Karla S., Vantourout, Julien C., Barton, Lisa M., Osswald, Heather L., Kato, Nobutaka, Gagaring, Kerstin, McNamara, Case W. +11 more·2019·Proceedings of the National Academy of Sciences

Published version of a preprint

Abstract

Significance: The combination of two newly emerging methods for chemical synthesis enables access to molecular space that was previously challenging or impossible to access. Thus, a C–H activation of ubiquitous carboxylic acids followed by their decarboxylative functionalization provides modular access to difunctionalized carbon frameworks with distinctly controlled stereochemistry. Application of this strategy to simplify the synthesis of medicinally important entities and to discover potent antimalarial compounds is described.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1073/pnas.1903048116

Cites

72 of 72 references verified0 citation errors · 0 not checkable

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • Several of the enantiopure fragment recognition groups deployed herein are poised for direct modification using synthetic methodologies such as C-H bond activation chemistry.

    “Toward this end, we note that the enantioprobes offer a convenient target engagement assay for assessing competitive binding of elaborated analogues in cells, and that several of the enantiopure fragment recognition groups deployed herein are poised for direct modification using synthetic methodologies such as C-H bond activation chemistry44–46.”

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Cites

Flagged first, then by citations

Cited by

Sorted by citations

Authors
Shang, M., Feu, K. S., Vantourout, J. C., Barton, L. M., Osswald, H. L., Kato, N., Gagaring, K., McNamara, C. W., Chen, G., Hu, L., Ni, S., Fernández-Canelas, P., Chen, M., Merchant, R. R., Qin, T., Schreiber, S. L., Melillo, B., Yu, J.-Q., & Baran, P. S.
Affiliations
  • Scripps Research Institute (US)
  • Broad Institute (US)
Corresponding author
  • Melillo, Bruno
  • Yu, Jin-Quan
  • Baran, Phil S.
Venue
Proceedings of the National Academy of Sciences
Published
2019-04-17
Volume
116
Issue
18
Pages
8721-8727
ISSN
  • 0027-8424 (ISSN-L)
  • 1091-6490
OpenAlex
W2937850742
Cited by
53
References
72
Citations by year
2026: 2 · 2025: 7 · 2024: 5 · 2023: 5 · 2022: 9 · 2021: 6 · 2020: 13 · 2019: 6
FWCI
3.33
Type
journal article
Language
en
Open access
Locations
  • Proceedings of the National Academy of Sciences (publishedVersion, cc-by)
  • ChemRxiv (acceptedVersion, cc-by-nc-nd)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • Royal College of Surgeons in Ireland (submittedVersion, cc-by-nc-nd)
Funders
  • HHS | National Institutes of Health (GM-118176)
  • Bill and Melinda Gates Foundation (OPP11823830)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Catalytic C–H Functionalization Methods
  • Physical Sciences › Chemistry › Organic Chemistry › Cyclopropane Reaction Mechanisms
  • Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
Keywords
C–H activation, decarboxylative coupling, alkyl carboxylic acids, asymmetric synthesis, stereocontrol, vicinal difunctionalization, modular synthesis, diversity-oriented synthesis, antimalarial compounds

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review