Evidence map›Paper›PMID 32831953›Full record

ArticleBeilstein journal of organic chemistry2020

Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination.

Yuqing Wang, Gaigai Wang, Anatoly A Peshkov, Ruwei Yao, Muhammad Hasan, Manzoor Zaman, Chao Liu, Stepan Kashtanov, Olga P Pereshivko, Vsevolod A Peshkov

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Article in Beilstein journal of organic chemistry, 2020. 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

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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. 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.

Yuqing WangCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P.R. China.
Gaigai WangCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P.R. China.
Anatoly A PeshkovDepartment of Chemistry, School of Science and Technology, Nazarbayev University, 53 Kabanbay Batyr Ave, Block 7, Nur-Sultan 010000, Republic of Kazakhstan.
Ruwei YaoCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P.R. China.
Muhammad HasanCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P.R. China.
Manzoor ZamanCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P.R. China.
Chao LiuCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P.R. China.
Stepan KashtanovDepartment of Chemistry, Xi'an Jiaotong-Liverpool University, Suzhou, 215123, P.R. China.
Olga P PereshivkoCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P.R. China.
Vsevolod A PeshkovCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P.R. China.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

In this report, we introduce a new strategy for controlling the stereochemistry in Ugi adducts. Instead of controlling stereochemistry directly during the Ugi reaction we have attempted to stereodefine the chiral center at the peptidyl position through the post-Ugi functionalization. In order to achieve this, we chose to study 2-oxo-aldehyde-derived Ugi adducts many of which partially or fully exist in the enol form that lacks the aforementioned chiral center. This in turn led to their increased nucleophilicity as compared to the standard Ugi adducts. As such, the stereocenter at the peptidyl position could be installed and stereodefined through the reaction with a suitable electrophile. Towards this end, we were able to deploy an asymmetric cinchona alkaloid-promoted electrophilic fluorination producing enantioenriched post-Ugi adducts fluorinated at the peptidyl position.

Indexed as

2-oxo-aldehydescinchona alkaloidselectrophilic fluorinationenantioselective synthesisUgi reaction

Identifiers

PMID32831953
PMCPMC7431756

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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.