Evidence map›Paper›PMID 27340456›Full record

ArticleBeilstein journal of organic chemistry2016

A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids.

Oksana S Mikhalchenko, Dina V Korchagina, Konstantin P Volcho, Nariman F Salakhutdinov

Abstract read
In one paragraph

Article in Beilstein journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Review
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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.

Oksana S Mikhalchenko1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, Lavrentiev ave., 9, 630090 Novosibirsk, Russian Federation.
Dina V Korchagina1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, Lavrentiev ave., 9, 630090 Novosibirsk, Russian Federation.
Konstantin P Volcho1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, Lavrentiev ave., 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova 2, 630090 Novosibirsk, Russian Federation.
Nariman F Salakhutdinov1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, Lavrentiev ave., 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova 2, 630090 Novosibirsk, Russian Federation.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Conditions enabling the single-step preparative synthesis of chiral 4-fluoropolyhydro-2H-chromenes in good yields through a reaction between monoterpenoid alcohols with para-menthane skeleton and aldehydes were developed for the first time. The BF3·Et2O/H2O system is used both as a catalyst and as a fluorine source. The reaction can involve aliphatic aldehydes as well as aromatic aldehydes containing various acceptor and donor substituents. 4-Hydroxyhexahydro-2H-chromenes were demonstrated to be capable of converting to 4-fluorohexahydro-2H-chromenes under the developed conditions, the reaction occurs with inversion of configuration.

Indexed as

chiralityfluorinehalo-Prins reactionisopulegolmonoterpene

Identifiers

PMID27340456
PMCPMC4902074

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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.