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Record W2029537522 · doi:10.1021/om991034m

Ruthenium Complexes with Novel Tridentate N<i>,</i>P<i>,</i>N Ligands Containing a Phosphonite Bridge between Two Chiral Oxazolines. Catalytic Activity in Cyclopropanation of Olefins and Transfer Hydrogenation of Acetophenone

2000· article· en· W2029537522 on OpenAlexaff
Pierre Braunstein, F. Naud, Andreas Pfaltz, Steven J. Rettig

Bibliographic record

VenueOrganometallics · 2000
Typearticle
Languageen
FieldChemistry
TopicAsymmetric Hydrogenation and Catalysis
Canadian institutionsUniversity of British Columbia
FundersCentre National de la Recherche ScientifiqueMinistère de l'Enseignement Supérieur et de la Recherche
KeywordsChemistrySteric effectsCyclopropanationLigand (biochemistry)Medicinal chemistryStereochemistryIsopropylOxazolineRutheniumAcetophenoneChiral ligandEthyleneCatalysisEnantioselective synthesisOrganic chemistry

Abstract

fetched live from OpenAlex

We compare the coordination behavior of the new chiral ligand ( S, S )-bis[1-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-methylethyl] phenylphosphonite ( V ), abreviated NOPON iPr and referred to as bis(oxazolinyl) phenylphosphonite, toward Ru(II) with that of NOPON Me 2 ( IV ). Although the similarity between IV and V led to the expectation that they would coordinate in a similar manner, considerable differences were observed. Whereas reaction of [RuCl 2 (η 6 - p -cymene)] 2 with IV afforded the pentacoordinated complex [RuCl 2 (NOPON Me 2 )] 1, the chiral ligand V led instead to the dinuclear, chloride-bridged complex [Ru(μ-Cl)Cl(NOPON i Pr )] 2 ( 3 ). The crystal structures of 1 and 3 have been determined by X-ray diffraction. The mer arrangement of the NOPON Me 2 ligand in 1 results from the presence of the four methyl groups, two of which would point toward each other and lead to a steric clash if a fac geometry were adopted. Preliminary theoretical calculations on 1 at the EHT level indicated that coordination of ethylene parallel to the RuCl 2 P plane would result in a stable situation and it is for steric reasons that ethylene does not coordinate to the metal, either parallel or perpendicular to the RuCl 2 P plane. Coordination of CO to 1 was found to be reversible, whereas bulkier ligands do not coordinate to Ru. Complex 3 is a rare example of a fully characterized complex in which a tridentate chiral bis(oxazoline)-type ligand coordinates in a non- mer fashion. It was evaluated in catalytic reactions such as asymmetric cyclopropanation of styrene with ethyl diazoacetate and transfer hydrogenation of acetophenone in propan-2-ol.

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)
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 score0.080
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)0.0000.000

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 head0.016
GPT teacher head0.238
Teacher spread0.222 · 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

Citations72
Published2000
Admission routes1
Has abstractyes

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