Evidence map›Paper›PMID 30779574›Full record

ArticleThe Journal of organic chemistry2019

Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives.

Bo Qu, Renchang Tan, Madison R Herling, Nizar Haddad, Nelu Grinberg, Marisa C Kozlowski, Xumu Zhang, Chris H Senanayake

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

8 authors.

Bo QuChemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road , Ridgefield , Connecticut 06877 , United States.ORCID 0000-0001-7347-0108
Renchang TanChemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road , Ridgefield , Connecticut 06877 , United States.
Madison R HerlingDepartment of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104 , United States.
Nizar HaddadChemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road , Ridgefield , Connecticut 06877 , United States.
Nelu GrinbergChemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road , Ridgefield , Connecticut 06877 , United States.
Marisa C KozlowskiDepartment of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104 , United States.ORCID 0000-0002-4225-7125
Xumu ZhangDepartment of Chemistry , Southern University of Science and Technology , Shenzhen , Guangdong 518055 , P.R. China.ORCID 0000-0001-5700-0608
Chris H SenanayakeChemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road , Ridgefield , Connecticut 06877 , United States.

Funding

Computational Methods for Selective CatalysisR01GM087605 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI KOZLOWSKI, MARISA C · 2010 to 2019
$2.4M
NIGMS NIH HHS R01 GM087605
6 · The paper itself

Abstract

Enantioenriched aldehydes are produced through asymmetric hydroformylation of styrene derivatives using BIBOP-type ligands. The featured example is enantioselective synthesis of 4-methyl-3,4-dihydroisocoumarin, which was prepared in a 95.1:4.9 enantiomeric ratio from asymmetric hydroformylation of ethyl 2-vinylbenzoate followed by in situ lactonization during the reduction process. The conditions are compatible with both electron-rich and electron-poor substituents.

Indexed as

AldehydesCoumarinsLigandsMolecular StructureStereoisomerismStyreneAldehydesCoumarinsLigandsStyrene

Identifiers

PMID30779574
PMCPMC6474792

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Registered trials

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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.