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Record W2164877636 · doi:10.1021/ol301506b

Short Synthesis of Enantiopure <i>trans</i>-3-Arylpiperazine-2-carboxylic Acid Derivatives via Diaza-Cope Rearrangement

2012· article· en· W2164877636 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

VenueOrganic Letters · 2012
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicSynthesis and Biological Activity
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsChemistryEnantiopure drugSodium periodatePiperazineTrifluoromethanesulfonateCarboxylic acidEthylenediamineRing (chemistry)RutheniumChlorideMedicinal chemistryStereochemistryOrganic chemistryCatalysisEnantioselective synthesis

Abstract

fetched live from OpenAlex

An efficient synthetic method was developed for the construction of enantiomerically pure trans-3-arylpiperazine-2-carboxylic acid derivatives using diaza-Cope rearrangement (DCR) as a key step starting from (R,R)/(S,S)-1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (HPEN). A complete transfer of stereochemical integrity was observed for the transformation. Piperazine ring formation from the chiral 1,2-ethylenediamine derivatives using diphenylvinylsulfonium triflate followed by oxidation using ruthenium(III) chloride monohydrate in the presence of sodium periodate provided the desired enantiopure trans-3-arylpiperazine-2-carboxylic acid derivatives.

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)0.000
metaresearch head score (Gemma)0.000
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 score0.050
Threshold uncertainty score0.675

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)0.0000.000

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 head0.010
GPT teacher head0.216
Teacher spread0.206 · 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