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Record W4412641844 · doi:10.1021/acs.orglett.5c02925

Strain Release Cycloadditions of 2H-Azirines: Access to Polycyclic Heterocycles

2025· article· en· W4412641844 on OpenAlexafffund
Kévin Lebair, Kaitlin A. Isfeld, Rebecca L. Davis, Thomas Poisson, Shawn K. Collins

Bibliographic record

VenueOrganic Letters · 2025
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Catalytic Reactions
Canadian institutionsUniversity of ManitobaUniversité de MontréalCentre in Green Chemistry and Catalysis
FundersNatural Sciences and Engineering Research Council of CanadaUniversité de RouenCentre National de la Recherche ScientifiqueNormandie UniversitéAgence Nationale de la RechercheFonds de recherche du Québec – Nature et technologiesRégion NormandieInstitut National des Sciences Appliquées RouenCanada Foundation for Innovation
KeywordsCycloadditionChemistryAzirineStrain (injury)Steric effectsSelectivityCombinatorial chemistryStereochemistryOrganic chemistryCatalysisRing (chemistry)

Abstract

fetched live from OpenAlex

A strain release cycloaddition has been developed that exploits intermediate azirines formed via irradiation with blue LEDs. Subsequent cycloaddition with pyrones afforded novel aza-heterocycles (13 examples, 42%→66% yields). A variety of substituents were tolerated. Computational analysis suggests a kinetically favored endo -[4 + 2]cycloaddition that occurs from the least sterically encumbered face of the azirine. Distortion/interaction analysis suggests that the energetic penalty associated with azirine deformation is the primary factor contributing to the observed selectivity.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.019
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0020.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.012
GPT teacher head0.259
Teacher spread0.247 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations0
Published2025
Admission routes2
Has abstractyes

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