Evidence map›Paper›PMID 38049954›Full record

ArticleJournal of the American Chemical Society2023

Highly Enantioselective 6π Photoelectrocyclizations Engineered by Hydrogen Bonding.

Wesley B Swords, Hanna Lee, Yerin Park, Franco Llamas, Kazimer L Skubi, Jiyong Park, Ilia A Guzei, Mu-Hyun Baik, Tehshik P Yoon

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

0numbers the graph read from it
0cells of the map it votes in
10citing 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

10 citing papers in PubMed.

  1. Article
  2. Bifunctional Photocatalysts: Exploiting Proximity for Enhanced Reaction Performance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
    Review
  3. Article
  4. Review
  5. Privileged Chiral Photocatalysts.Angewandte Chemie (International ed. in English) · 2025
    Review
  6. Article
  7. Article
  8. Article
  9. Article
  10. 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

9 authors.

Wesley B SwordsDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0002-2986-326X
Hanna LeeDepartment of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.ORCID 0000-0002-7391-6138
Yerin ParkDepartment of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.
Franco LlamasDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Kazimer L SkubiDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0002-9689-1842
Jiyong ParkDepartment of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.ORCID 0000-0002-3225-4510
Ilia A GuzeiDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0003-1976-7386
Mu-Hyun BaikDepartment of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.ORCID 0000-0002-8832-8187
Tehshik P YoonDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0002-3934-4973

Funding

Laser-Enhanced NMR Instrumentation for Chemical and Biochemical ResearchS10OD012245 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI CAVAGNERO, SILVIA · 2013 to 2013
$1.0M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
A General Co-Catalytic Methodology for Enantioselective Photoredox Radical Cation ReactionsF32GM134611 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI SWORDS, WESLEY BRYAN · 2019 to 2021
$160k
NIGMS NIH HHS F32 GM134611NIH HHS S10 OD012245NIH HHS S10 OD020022
6 · The paper itself

Abstract

Photochemical electrocyclization reactions are valued for both their ability to produce structurally complex molecules and their central role in elucidating fundamental mechanistic principles of photochemistry. We present herein a highly enantioselective 6π photoelectrocyclization catalyzed by a chiral Ir(III) photosensitizer. This transformation was successfully realized by engineering a strong hydrogen-bonding interaction between a pyrazole moiety on the catalyst and a basic imidazolyl ketone on the substrate. To shed light on the origin of stereoinduction, we conducted a comprehensive investigation combining experimental and computational mechanistic studies. Results from density functional theory calculations underscore the crucial role played by the prochirality and the torquoselectivity in the electrocyclization process as well as the steric demand in the subsequent [1,4]-H shift step. Our findings not only offer valuable guidance for developing chiral photocatalysts but also serve as a significant reference for achieving high levels of enantioselectivity in the 6π photoelectrocyclization reaction.

Identifiers

PMID38049954
PMCPMC10842740

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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.