Evidence map›Paper›PMID 34123197›Full record

ArticleChemical science2020

Enantioselective synthesis of highly oxygenated acyclic quaternary center-containing building blocks

Aurapat Ngamnithiporn, Toshihiko Iwayama, Michael D Bartberger, Brian M Stoltz

Abstract read
In one paragraph

Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Article
  2. 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.

Aurapat NgamnithipornWarren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.ORCID https://orcid.org/0000-0002-5389-8171
Toshihiko IwayamaWarren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.
Michael D Bartberger1200 Pharma LLC 844 East Green Street, Suite 204 Pasadena CA 91101 USA.ORCID https://orcid.org/0000-0002-5167-3139
Brian M StoltzWarren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.ORCID https://orcid.org/0000-0001-9837-1528

Funding

The Synthesis of Bioactive Polycyclic Natural ProductsR01GM080269 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI STOLTZ, BRIAN M · 2007 to 2022
$5.0M
NIGMS NIH HHS R01 GM080269
6 · The paper itself

Abstract

The development of a palladium-catalyzed enantioselective decarboxylative allylic alkylation of cyclic siloxyketones to produce enantioenriched silicon-tethered heterocycles is reported. The reaction proceeds smoothly to provide products bearing a quaternary stereocenter in excellent yields (up to 91% yield) with high levels of enantioselectivity (up to 94% ee). We further utilized the unique reactivity of the siloxy functionality to access chiral, highly oxygenated acyclic quaternary building blocks. In addition, we subsequently demonstrated the utility of these compounds through the synthesis of a lactone bearing vicinal quaternary-trisubstituted stereocenters.

Identifiers

PMID34123197
PMCPMC8162308

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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.