MétaCan
Menu
Back to cohort
Record W4280586762 · doi:10.1002/chem.202201438

Catalytic Asymmetric Syntheses of Alkylidenecyclopropanes from Allenoates with Donor‐Acceptor and Diacceptor Diazo Reagents

2022· article· en· W4280586762 on OpenAlexaff
Yoko Hasegawa, Thomas Cantin, Jonathan Decaens, Samuel Couve‐Bonnaire, André B. Charette, Thomas Poisson, Philippe Jubault

Bibliographic record

VenueChemistry - A European Journal · 2022
Typearticle
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsUniversité de MontréalCentre in Green Chemistry and Catalysis
FundersAgence Nationale de la Recherche
KeywordsDiazoCyclopropanationEnantioselective synthesisIntramolecular forceChemistryCatalysisReagentYield (engineering)Electron acceptorAcceptorMedicinal chemistryCombinatorial chemistryOrganic chemistryMaterials science

Abstract

fetched live from OpenAlex

Abstract The first diastereo‐ and enantioselective cyclopropanation reactions of electron‐deficient allenes with donor‐acceptor and diacceptor diazo reagents are described. The desired enantioenriched alkylidenecyclopropanes (ACPs) were obtained in high yields with high diastereo‐ and enantioselectivities in the presence of Rh 2 (( S )‐TCPTAD) 4 or Rh 2 (( R )‐BTPCP) 4 catalysts (up to 95 % yield, >95 : 5 d.r. and 99 : 1 e.r.). This methodology gave a direct access to ACPs bearing multiple electron‐deficient substituents and allows to further expand the availability of ACPs chemistry. Interestingly, during the examination of the scope of this reaction, the asymmetric intramolecular C−H insertion reaction into tert ‐butyl group was observed as a side reaction with up to 94 : 6 e.r.

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 score0.073
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
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 head0.013
GPT teacher head0.195
Teacher spread0.182 · 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

Citations10
Published2022
Admission routes1
Has abstractyes

Explore more

Same venueChemistry - A European JournalSame topicCyclopropane Reaction MechanismsFrench-language works237,207