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Record W2054976157 · doi:10.1021/ja077463q

Highly Chemoselective Metal-Free Reduction of Tertiary Amides

2007· article· en· W2054976157 on OpenAlexaff
Guillaume Barbe, André B. Charette

Bibliographic record

VenueJournal of the American Chemical Society · 2007
Typearticle
Languageen
FieldChemistry
TopicAdvanced Synthetic Organic Chemistry
Canadian institutionsUniversité de Montréal
Fundersnot available
KeywordsChemistryReduction (mathematics)Tertiary amineFunctional groupChemical reductionTertiary alcoholsOrganic chemistryChemoselectivityMetalCombinatorial chemistryCatalysis

Abstract

fetched live from OpenAlex

This communication describes the chemoselective metal-free reduction of tertiary amides to the corresponding amines. Hantzsch ester is used as a mild reducing agent for the reduction of trifluoromethanesulfonic anhydride activated amides providing the tertiary amines with high functional group tolerance.

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

Direct model labels (unvalidated)

Per-model category and study-design labels from the labeling rounds. They are machine output, unvalidated, and the disagreement between models ships as data. No study design here is MEDLINE-validated yet.

Model armCategoriesStudy designConfidence
gptno category
Domain: not available · Genre: Methods
About the Canadian research system: no · About a Canadian topic: no
Bench or experimentalhigh
grokno category
Domain: not available · Genre: Empirical
About the Canadian research system: no · About a Canadian topic: no
Bench or experimentalhigh
opusno category
Domain: not available · Genre: Empirical
About the Canadian research system: no · About a Canadian topic: no
Bench or experimentalhigh
models agreeAgreement compares identical category sets and study designs across arms.

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 score0.001
Threshold uncertainty score0.000

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
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)0.0010.001

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 head0.006
GPT teacher head0.240
Teacher spread0.235 · 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

Labeled directly by 3 models reading the full record.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreMethods · Empirical

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

Citations263
Published2007
Admission routes1
Has abstractyes

Explore more

Same venueJournal of the American Chemical SocietySame topicAdvanced Synthetic Organic ChemistryFrench-language works237,207