MétaCan
Menu
Back to cohort
Record W4386255312 · doi:10.26434/chemrxiv-2023-vt063

Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds

2023· preprint· en· W4386255312 on OpenAlexafffund
Kyla Woelk, Kushal Dhake, Nathan D. Schley, David C. Leitch

Bibliographic record

VenueChemRxiv · 2023
Typepreprint
Languageen
FieldChemistry
TopicSynthetic Organic Chemistry Methods
Canadian institutionsUniversity of Victoria
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsBCH codeIntramolecular forceChemistryGlycineArylBicyclic moleculeCombinatorial chemistryStereochemistryMathematicsAmino acidOrganic chemistryDecoding methodsAlgorithm

Abstract

fetched live from OpenAlex

We report the synthesis of 2-oxo-bicyclo[2.1.1]hexanes (2-oxo-BCHs) from bicyclobutanes (BCBs) and readily available enolate precursors. We propose this reaction proceeds via initial enolate addition to the bicyclobutane, followed by an intramolecular acyl substitution by the resulting enolate intermediate. Glycine-derived enolates directly give protected 2-oxo-3-amino-BCH derivatives that can be further functionalized. Arylacetate derivatives are also suitable enolate precursors, giving 2-oxo-3-aryl-BCH scaffolds from readily available starting materials.

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)0.001
metaresearch head score (Gemma)0.002
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesInsufficient payload (model declined to judge)
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 score0.034
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.002
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0010.000
Open science0.0030.005
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0090.001

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 head0.072
GPT teacher head0.343
Teacher spread0.271 · 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; both teacher heads agree on what is shown here.

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

Citations1
Published2023
Admission routes2
Has abstractyes

Explore more

Same venueChemRxivSame topicSynthetic Organic Chemistry MethodsFrench-language works237,207