Evidence map›Paper›PMID 41565835›Full record

ArticleNature chemistry2026

Hyperpyramidalized alkenes with bond orders near 1.5 as synthetic building blocks.

Jiaming Ding, Sarah A French, Christina A Rivera, Arismel Tena Meza, Dominick C Witkowski, K N Houk, Neil K Garg

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Nature chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing 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

1 citing paper in PubMed.

  1. Rule-breaking in chemical synthesis.Science advances · 2026
    Review
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

7 authors.

Jiaming Ding *Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA.ORCID http://orcid.org/0000-0003-4284-5274
Sarah A French *Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA.ORCID http://orcid.org/0000-0003-2089-3857
Christina A RiveraDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA.ORCID http://orcid.org/0000-0002-1588-7017
Arismel Tena MezaDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA.
Dominick C WitkowskiDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA.ORCID http://orcid.org/0000-0001-5692-6548
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA.
Neil K GargDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA. neilgarg@ucla.edu.ORCID http://orcid.org/0000-0002-7793-2629

Funding

Exploiting Unconventional Building Blocks in Chemical SynthesisR35GM139593 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI Neil K. Garg · 2021 to 2026
$4.0M
NMR Console and Prodigy CryoProbeS10OD028644 · OD · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI GARG, NEIL K · 2021 to 2021
$600k
Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical ResearchS10RR025631 · NCRR · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N · 2009 to 2009
$328k
Enantioselective Reactions with Amide Electrophiles Utilizing Transition-Metal CatalysisF31GM149161 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI TENA-MEZA, ARISMEL · 2023 to 2025
$86k
National Science Foundation (NSF) CHE-1048804National Science Foundation (NSF) CHE-2153972National Science Foundation (NSF) OCI-1053575NCRR NIH HHS S10 RR025631NIGMS NIH HHS F31 GM149161NIGMS NIH HHS R35 GM139593NIH HHS S10 OD028644U.S. Department of Energy (DOE) DE-FC02-02ER63421U.S. Department of Health & Human Services | National Institutes of Health (NIH) S10OD028644U.S. Department of Health & Human Services | NIH | National Center for Research Resources (NCRR) S10RR025631
6 · The paper itself

Abstract

Alkenes typically have trigonal planar geometries at each terminus, with favourable σ- and π-bonding leading to a bond order of ~2. Here we consider unusual alkenes that possess an extreme form of geometric distortion, termed hyperpyramidalization. In a hyperpyramidalized alkene, geometries deviate remarkably from the typical trigonal planar alkene geometry, leading to weak π-bonding and abnormal alkene bond orders approaching 1.5. Cubene and 1,7-quadricyclene, first validated in 1988 and 1979, respectively, but overlooked for decades since, are the focus of the present study. We leverage their unusually weak π-bonds in cycloadditions, enabling the construction of complex scaffolds and access to previously unrealized chemical space. The origins of the unusually low bond orders were investigated using computational methods. These efforts are expected to prompt future studies of molecules that display hyperpyramidalization or atypical bond orders.

Identifiers

PMID41565835
PMCPMC12859755

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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.