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Record W4411376073 · doi:10.1021/acsorginorgau.5c00038

Noyori–Ikariya Asymmetric Transfer Hydrogenation of Prochiral α-CF<sub>3</sub> and α-SF<sub>5</sub> Ketones

2025· article· en· W4411376073 on OpenAlexafffund
Kelly Burchell-Reyes, Chloé Depoumps, Jean‐François Paquin

Bibliographic record

VenueACS Organic & Inorganic Au · 2025
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicFluorine in Organic Chemistry
Canadian institutionsUniversité Laval
FundersNatural Sciences and Engineering Research Council of CanadaFonds de recherche du Québec – Nature et technologiesUniversité Laval
KeywordsEnantioselective synthesisChemistryTransfer hydrogenationElectronegativitySteric effectsTrifluoromethylEnantiomerLipophilicityKetoneNoyori asymmetric hydrogenationStereoisomerismAsymmetric hydrogenationOrganic chemistryCombinatorial chemistryCatalysisStereochemistryAlkyl

Abstract

fetched live from OpenAlex

High Resolution Image Download MS PowerPoint Slide As the demand for both fluoropharmaceuticals and single enantiomer drugs increases, there is a need for enantioselective synthetic methods toward chiral fluorinated molecules. Trifluoromethyl (CF 3 ) and the emerging pentafluorosulfanyl (SF 5 ) fluorinated groups bear characteristic high electronegativity and lipophilicity, while exhibiting distinct steric properties, which make them attractive substituents in drug discovery. Our group's previous exploration of the gold-catalyzed hydration of CF 3 - and SF 5 -alkynes to furnish the corresponding α-CF 3 - and α-SF 5 -ketones presents an accessible springboard for the enantioselective synthesis of β-CF 3 and β-SF 5 alcohols. To this end, Noyori–Ikariya asymmetric transfer hydrogenation (ATH) conditions afforded high enantioselectivity (up to 96% ee) and yields (up to 84%) across a scope of eight CF 3 and six SF 5 substrates.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
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 score0.002
Threshold uncertainty score0.006

Distilled classifier scores by category (both heads)

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 integrity0.0000.001
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 head0.029
GPT teacher head0.318
Teacher spread0.289 · 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 source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
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".

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Citations0
Published2025
Admission routes2
Has abstractyes

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Same venueACS Organic & Inorganic AuSame topicFluorine in Organic ChemistryFrench-language works237,207