Evidence map›Paper›PMID 31460756›Full record

ArticleJournal of the American Chemical Society2019

Enantioselective Alkylation of 2-Alkylpyridines Controlled by Organolithium Aggregation.

Joshua J Gladfelder, Santanu Ghosh, Maša Podunavac, Andrew W Cook, Yun Ma, Ryan A Woltornist, Ivan Keresztes, Trevor W Hayton, David B Collum, Armen Zakarian

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Breaking theJournal of the American Chemical Society · 2023
    Article
  6. 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

10 authors.

Joshua J GladfelderDepartment of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
Santanu GhoshDepartment of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
Maša PodunavacDepartment of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
Andrew W CookDepartment of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
Yun MaDepartment of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
Ryan A WoltornistDepartment of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States.
Ivan KeresztesDepartment of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States.
Trevor W HaytonDepartment of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.ORCID 0000-0003-4370-1424
David B CollumDepartment of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States.ORCID 0000-0001-6065-1655
Armen ZakarianDepartment of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.ORCID 0000-0002-9120-1232

Funding

Total synthesis of bioactive natural productsR01GM077379 · NIGMS · UNIVERSITY OF CALIFORNIA SANTA BARBARA · PI SERVENT, DENIS, ZAKARIAN, ARMEN · 2008 to 2021
$5.3M
Alkali Metal Chemistry-Structures, Mechanisms, and ApplicationsR35GM131713 · NIGMS · CORNELL UNIVERSITY · PI COLLUM, DAVID B. · 2019 to 2023
$2.8M
NIGMS NIH HHS R01 GM077379
6 · The paper itself

Abstract

Direct enantioselective α-alkylation of 2-alkylpyridines provides access to chiral pyridines via an operationally simple protocol that obviates the need for prefunctionalization or preactivation of the substrate. The alkylation is accomplished using chiral lithium amides as noncovalent stereodirecting auxiliaries. Crystallographic and solution NMR studies provide insight into the structure of well-defined chiral aggregates in which a lithium amide reagent directs asymmetric alkylation.

Indexed as

AlkylationLithiumMolecular StructureOrganometallic CompoundsPyridinesStereoisomerismLithiumOrganometallic CompoundsPyridines

Identifiers

PMID31460756
PMCPMC7412967

What OpenQuestion holds

Textmetadata
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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.