Evidence map›Paper›PMID 33766881›Full record

ArticleScience (New York, N.Y.)2021

Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes.

Jiajia Ma, Shuming Chen, Peter Bellotti, Renyu Guo, Felix Schäfer, Arne Heusler, Xiaolong Zhang, Constantin Daniliuc, M Kevin Brown, Kendall N Houk and 1 more

Abstract read
In one paragraph

Article in Science (New York, N.Y.), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 70 papers.

0numbers the graph read from it
0cells of the map it votes in
70citing 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

70 citing papers in PubMed.

  1. A Unified Approach for the Synthesis of Conformationally Locked and spChemistry (Weinheim an der Bergstrasse, Germany) · 2026
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10 more citing papers are in PubMed but not listed here.

4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

11 authors.

Jiajia Ma *Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.ORCID https://orcid.org/0000-0002-4339-0462
Shuming Chen *Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA.
Peter Bellotti *Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.ORCID https://orcid.org/0000-0001-9367-5100
Renyu GuoDepartment of Chemistry, Indiana University, Bloomington, IN 47405, USA.
Felix SchäferOrganisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.
Arne HeuslerOrganisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.ORCID https://orcid.org/0000-0002-5092-4047
Xiaolong ZhangOrganisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.ORCID https://orcid.org/0000-0003-4695-5884
Constantin DaniliucOrganisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.ORCID https://orcid.org/0000-0002-6709-3673
M Kevin BrownDepartment of Chemistry, Indiana University, Bloomington, IN 47405, USA. brownmkb@indiana.edu houk@chem.ucla.edu glorius@uni-muenster.de.ORCID https://orcid.org/0000-0002-4993-0917
Kendall N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA. brownmkb@indiana.edu houk@chem.ucla.edu glorius@uni-muenster.de.ORCID https://orcid.org/0000-0002-8387-5261
Frank GloriusOrganisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany. brownmkb@indiana.edu houk@chem.ucla.edu glorius@uni-muenster.de.ORCID https://orcid.org/0000-0002-0648-956X

Funding

Methods and Strategies for Chemical SynthesisR35GM131755 · NIGMS · TRUSTEES OF INDIANA UNIVERSITY · PI Michael Kevin Brown · 2019 to 2026
$4.0M
European Research Council 788558NIGMS NIH HHS R35 GM131755
6 · The paper itself

Abstract

Dearomative cycloaddition reactions represent an ideal means of converting flat arenes into three-dimensional architectures of increasing interest in medicinal chemistry. Quinolines, isoquinolines, and quinazolines, despite containing latent diene and alkene subunits, are scarcely applied in cycloaddition reactions because of the inherent low reactivity of aromatic systems and selectivity challenges. Here, we disclose an energy transfer-mediated, highly regio- and diastereoselective intermolecular [4 + 2] dearomative cycloaddition reaction of these bicyclic azaarenes with a plethora of electronically diverse alkenes. This approach bypasses the general reactivity and selectivity issues, thereby providing various bridged polycycles that previously have been inaccessible or required elaborate synthetic efforts. Computational studies with density functional theory elucidate the mechanism and origins of the observed regio- and diastereoselectivities.

Indexed as

Cycloaddition ReactionAlkenesCatalysisEnergy TransferHydrocarbons, AromaticMolecular StructureQuinolinesStereoisomerismAlkenesHydrocarbons, AromaticQuinolines

Identifiers

PMID33766881
PMCPMC7610643

What OpenQuestion holds

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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.