Evidence map›Paper›PMID 35167300›Full record

ArticleThe Journal of organic chemistry2022

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides.

Nicole D Bartolo, Krystyna M Demkiw, Jacquelyne A Read, Elizabeth M Valentín, Yingying Yang, Alexandra M Dillon, Chunhua T Hu, Michael D Ward, K A Woerpel

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
  2. Hydrogen-bonded frameworks for conformational analysis of reactive substrates.Chemical communications (Cambridge, England) · 2024
    Article
  3. Article
  4. 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

9 authors.

Nicole D BartoloDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0002-9907-7774
Krystyna M DemkiwDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0001-5457-3291
Jacquelyne A ReadDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0002-0681-7703
Elizabeth M ValentínSt. Mary's College of California, 1928 St. Marys Road, Moraga, California 94575, United States.ORCID 0000-0002-8516-1369
Yingying YangDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.
Alexandra M DillonDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0003-4680-0284
Chunhua T HuDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0002-8172-2202
Michael D WardDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0002-2090-781X
K A WoerpelDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0002-8515-0301

Funding

Stereoselective Reactions of Oxocarbenium Ions and Related IntermediatesR01GM129286 · NIGMS · NEW YORK UNIVERSITY · PI WOERPEL, KEITH ALLEN · 2018 to 2021
$1.2M
Acquisition of a Cryoprobe for a 600 MHz NMR SpectrometerS10OD016343 · OD · NEW YORK UNIVERSITY · PI KROGSGAARD, MICHELLE, TRAASETH, NATHANIEL J. · 2014 to 2014
$360k
NIGMS NIH HHS R01 GM129286NIH HHS S10 OD016343
6 · The paper itself

Abstract

The addition of the highly reactive reagent allylmagnesium halide to α-substituted acyclic chiral ketones proceeded with high stereoselectivity. The stereoselectivity cannot be analyzed by conventional stereochemical models because these reactions do not conform to the requirements of those models. Instead, the stereoselectivity arises from the approach of the nucleophile to the most accessible diastereofaces of the lowest-energy conformations of the ketones. High stereoselectivity is expected, and the stereochemical outcome can be predicted, with conformationally biased ketones that have sterically distinguishable diastereofaces wherein only one face is accessible for nucleophilic addition. The conformations of the ketones can be determined by a combination of computational modeling and, in some cases, structure determination by X-ray crystallography.

Indexed as

KetonesIndicators and ReagentsMolecular ConformationStereoisomerismIndicators and ReagentsKetones

Identifiers

PMID35167300
PMCPMC9022492

What OpenQuestion holds

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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.