MétaCan
Menu
Back to cohort
Record W4409059446 · doi:10.1021/acs.orglett.5c00852

Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I<sup>(III)</sup>/S<sup>(VI)</sup> Ylides

2025· article· en· W4409059446 on OpenAlexaff
Shang‐Shi Zhang, Jiaohang Wei, Qiong Hu, Zifeng Yang, Wen‐Xuan Zou, Dan‐Ting Shen, Mei-Zhu Bao, Xiang Liu

Bibliographic record

VenueOrganic Letters · 2025
Typearticle
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsCentre for Drug Research and Development
FundersGuangzhou Municipal Science and Technology ProjectGuangdong Pharmaceutical UniversityNational Natural Science Foundation of China
KeywordsChemistrySigmatropic reactionAlkylationHydroxylationMedicinal chemistryStereochemistryOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation of I (III) /S (VI) ylides with 1,3-dicarbonyls. By slight modification of the reaction conditions, controllable alkylation-hydroxylation and dialkylation of I (III) /S (VI) ylides were achieved. This strategy affords a diverse array of α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement in the [1,2]-sigmatropic rearrangement of sulfoxonium ylides and highlight the divergent reactivity of I (III) /S (VI) ylides.

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)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
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 score0.024
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0040.000

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 head0.007
GPT teacher head0.210
Teacher spread0.204 · 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 teacher head, not a consensus.

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

Citations4
Published2025
Admission routes1
Has abstractyes

Explore more

Same venueOrganic LettersSame topicCyclopropane Reaction MechanismsFrench-language works237,207