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Record W4416724531 · doi:10.1021/acs.orglett.5c04430

Synthesis of Spiroindenes via Palladium Catalysis Using Oxabicycles as Acetylene Surrogates

2025· article· en· W4416724531 on OpenAlexafffund
Clara Jans, Armaan Grewal, Xavier Abel‐Snape, Lorenzo Rizzo, Gregory Hughes, Mark Lautens

Bibliographic record

VenueOrganic Letters · 2025
Typearticle
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversity of Toronto
FundersUniversity of TorontoMinistero dell’Istruzione, dell’Università e della RicercaNatural Sciences and Engineering Research Council of CanadaMerck
KeywordsAcetyleneCatalysisPalladiumLewis acids and basesMoleculePalladium catalyst

Abstract

fetched live from OpenAlex

We report the palladium-catalyzed synthesis of spiroindenes using oxabicycles as acetylene surrogates. This protocol allows for the synthesis of a diverse library of heterocyclic-tethered spiroindenes. Preliminary results using enantioenriched oxabicycles as chiral auxiliaries allow for the synthesis of enantioenriched spiroindenes. The formation of unusual 6- endo - trig naphthyl side products is observed for substrates with proximal Lewis basic nitrogens.

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 score0.006
Threshold uncertainty score1.000

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)0.0010.000

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 head0.008
GPT teacher head0.248
Teacher spread0.240 · 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

Citations2
Published2025
Admission routes2
Has abstractyes

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