Evidence map›Paper›PMID 34593790›Full record

ArticleNature communications2021

Chiral Brønsted acid-controlled intermolecular asymmetric [2 + 2] photocycloadditions.

Evan M Sherbrook, Matthew J Genzink, Bohyun Park, Ilia A Guzei, Mu-Hyun Baik, Tehshik P Yoon

Abstract read
In one paragraph

Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.

0numbers the graph read from it
0cells of the map it votes in
22citing 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

22 citing papers in PubMed.

  1. Article
  2. Article
  3. Fused 3D boron heterocyclesChemical science · 2026
    Article
  4. Article
  5. Review
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  7. Article
  8. Article
  9. Article
  10. Highly acidicChemical science · 2024
    Article
  11. Article
  12. Review
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Cooperative Stereoinduction in Asymmetric Photocatalysis.Journal of the American Chemical Society · 2022
    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

6 authors.

Evan M SherbrookDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin, 53706, USA.ORCID 0000-0003-4765-5314
Matthew J GenzinkDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin, 53706, USA.ORCID 0000-0002-8956-5635
Bohyun ParkDepartment of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Republic of Korea.ORCID 0000-0003-0552-8763
Ilia A GuzeiDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin, 53706, USA.ORCID 0000-0003-1976-7386
Mu-Hyun BaikDepartment of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Republic of Korea. mbaik2805@kaist.ac.kr.ORCID 0000-0002-8832-8187
Tehshik P YoonDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin, 53706, USA. tyoon@chem.wisc.edu.ORCID 0000-0002-3934-4973

Funding

ENANTIOSELECTIVE TRIPLET SENSITIZATION REACTIONSR01GM127545 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI YOON, TEHSHIK P · 2018 to 2021
$1.2M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
NIGMS NIH HHS R01 GM127545NIH HHS S10 OD020022
6 · The paper itself

Abstract

Control over the stereochemistry of excited-state photoreactions remains a significant challenge in organic synthesis. Recently, it has become recognized that the photophysical properties of simple organic substrates can be altered upon coordination to Lewis acid catalysts, and that these changes can be exploited in the design of highly enantioselective catalytic photoreactions. Chromophore activation strategies, wherein simple organic substrates are activated towards photoexcitation upon binding to a Lewis acid catalyst, rank among the most successful asymmetric photoreactions. Herein, we show that chiral Brønsted acids can also catalyze asymmetric excited-state photoreactions by chromophore activation. This principle is demonstrated in the context of a highly enantio- and diastereoselective [2+2] photocycloaddition catalyzed by a chiral phosphoramide organocatalyst. Notably, the cyclobutane products arising from this method feature a trans-cis stereochemistry that is complementary to other enantioselective catalytic [2+2] photocycloadditions reported to date.

Indexed as

LightCatalysisCycloaddition ReactionMolecular StructureStereoisomerism

Identifiers

PMID34593790
PMCPMC8484615

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.