Evidence map›Paper›PMID 27956752›Full record

ArticleTetrahedron letters2016

Functionalizing the γ-Position of α-Diazo-β-ketoesters.

Thu Q Nguyen, Maha Alqurafi, Cash Edwards, Pauline Nguyen, Jean Kim, Samuel Casco, Maricka Bennet, Christopher Chiang, Maureen Lohry, Melina Cox and 6 more

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Tetrahedron letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing 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

1 citing paper in PubMed.

  1. 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

16 authors.

Thu Q NguyenDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Maha AlqurafiDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Cash EdwardsDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Pauline NguyenDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Jean KimDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Samuel CascoDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Maricka BennetDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Christopher ChiangDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Maureen LohryDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Melina CoxDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Byron MeshramDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Duyen LeDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Eugene KimDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Snigdha SmritiDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.
Peter OelschlaegerDepartment of Pharmaceutical Sciences, College of Pharmacy, Western University of Health Sciences, 309 East Second St., Pomona, California, 91768, USA.
John D BuynakDepartment of Chemistry, Southern Methodist University, Dallas, TX, 75275-0314 USA.

Funding

Bicyclic beta-Lactam Antibiotics as Poor Substrates for Metallo-beta-lactamasesR15AI109624 · NIAID · SOUTHERN METHODIST UNIVERSITY · PI BUYNAK, JOHN D · 2014 to 2014
$438k
NIAID NIH HHS R15 AI109624
6 · The paper itself

Abstract

Although α-diazo-β-ketoesters are synthetically versatile intermediates, methodology for introducing this functionality into complex molecules is still limited, most frequently involving a carboxylic acid precursor, which is then activated and transformed into a β-ketoester, with the diazo group being subsequently added with a diazo transfer reagent. While introducing this highly functional moiety in a convergent one step process would be ideal, such an objective is limited by the relatively few studies which address functionalization of the α-diazo-β-ketoester at the γ-position. In the present investigation, we evaluate strategies, both new and established, for functionalizing α-diazo-β-ketoesters, particularly with regard to generating compounds prospectively useful in the synthesis of C1-substituted carbapenems. We report the first δ-aldehydo-α-diazo-β-ketoester as well as a method for its oxidation to the corresponding methyl ester, and the formation of a new substituted pyrazole under basic conditions.

Indexed as

carbapenemDiazopyrazoleβ-ketoester

Identifiers

PMID27956752
PMCPMC5147747

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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.