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Record W2949070094 · doi:10.1021/ja027474d

The Development of a Catalytic Synthesis of Münchnones:  A Simple Four-Component Coupling Approach to α-Amino Acid Derivatives

2003· article· en· W2949070094 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueJournal of the American Chemical Society · 2003
Typearticle
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsMcGill University
Fundersnot available
KeywordsChemistryImineCarbon monoxideCatalysisChlorideCombinatorial chemistryAmino acidOrganic chemistryAlcoholPalladium

Abstract

fetched live from OpenAlex

A new palladium-catalyzed route to prepare 1,3-oxazolium-5-oxides (i.e., Münchnones) directly from imine, carbon monoxide, and acid chloride building blocks has been developed. This provides a straightforward catalytic synthesis of Münchnones and is amenable to generating a diverse range of products by simple modification of the imine or acid chloride starting materials. Münchnones are vital synthetic intermediates to a variety of heterocyclic and peptide-based molecules. As such, this methodology has been utilized to design a new catalytic synthesis of alpha-amino acid derivatives via a one-pot coupling of imines, carbon monoxide, and acid chloride followed by alcohol. The latter represents the first reported catalytic synthesis of alpha-amino acids directly from imine and carbon monoxide building blocks.

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.

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)0.001
Version: codex-gemma-dda1882f352aValidation 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 score0.007
Threshold uncertainty score0.522

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.001
Bibliometrics0.0000.000
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

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 head0.022
GPT teacher head0.265
Teacher spread0.244 · 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