Evidence map›Paper›PMID 34399579›Full record

ArticleThe Journal of organic chemistry2021

Sequential Norrish-Yang Cyclization and C-C Cleavage/Cross-Coupling of a [4.1.0] Fused Saturated Azacycle.

Charis Amber, Bohyun Park, Li-Ping Xu, Jose B Roque, Charles S Yeung, Djamaladdin G Musaev, Richmond Sarpong, Rebecca Lyn LaLonde

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Article
  2. Skeletal Editing Strategies Driven by Total Synthesis.Accounts of chemical research · 2025
    Article
  3. Article
  4. Synthesis of Cycloheptatriene-Containing Azetidine Lactones.The Journal of organic chemistry · 2022
    Article
  5. 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

8 authors.

Charis AmberDepartment of Chemistry, University of California, Berkeley, California 94720, United States.
Bohyun ParkDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0000-0003-0552-8763
Li-Ping XuCherry L. Emerson Center for Scientific Computation and Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.ORCID 0000-0001-6421-062X
Jose B RoqueDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0000-0002-5449-1584
Charles S YeungDisruptive Chemistry Fellow, Department of Discovery Chemistry, Merck & Company, Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID 0000-0001-7320-7190
Djamaladdin G MusaevCherry L. Emerson Center for Scientific Computation and Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.ORCID 0000-0003-1160-6131
Richmond SarpongDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0000-0002-0028-6323
Rebecca Lyn LaLondeChemistry Department, Reed College, Portland, Oregon 97202, United States.ORCID 0000-0001-7062-0166

Funding

Strategies and Methods for Complex Molecule Synthesis: Acquisition of a 400 MHz Nuclear Magnetic Resonance Spectrometer ConsoleR35GM130345 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI Richmond Sarpong · 2019 to 2026
$5.4M
Acquisition of a Cryoprobe and Related Accessories for a 600 MHz NMR Spectrometer to Support Health Research Activities at the University of California, BerkeleyS10OD024998 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI HARTWIG, JOHN F · 2018 to 2018
$265k
NIGMS NIH HHS R35 GM130345NIH HHS S10 OD024998
6 · The paper itself

Abstract

Methods that functionalize the periphery of azacylic scaffolds have garnered increasing interest in recent years. Herein, we investigate the selectivity of a solid-state Norrish-Yang cyclization (NYC) and subsequent C-C cleavage/cross-coupling reaction of a strained cyclopropane-fused azacyclic system. Surprisingly, the NYC primarily furnished a single lactam constitutional and diastereo-isomer. The regioselectivity of the C-C cleavage of the α-hydroxy-β-lactam moiety could be varied by altering the ligand set used in the coupling chemistry. Experimental and computational observations are discussed.

Indexed as

beta-LactamsCyclizationPhysical PhenomenaStereoisomerismbeta-Lactams

Identifiers

PMID34399579
PMCPMC8627179

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.