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Record W4381734583 · doi:10.1055/s-0040-1720074

Hemiboronic Acid-Catalyzed Reduction of α,β-Unsaturated Ketones with Reagent-Controlled Chemoselectivity

2023· article· en· W4381734583 on OpenAlexfundno aff
Dennis G. Hall, Jason P. G. Rygus, Daniel B. Boateng

Bibliographic record

VenueSynlett · 2023
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsnot available
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryChemoselectivityCatalysisKetoneBoraneDeoxygenationSelective reductionCationic polymerizationReagentSilaneSelectivityOrganic chemistryCombinatorial chemistry

Abstract

fetched live from OpenAlex

Abstract The use of an air-stable cationic hemiboronic acid catalyst for the chemoselective reduction of enones is described. By changing the identity and stoichiometry of the silane reducing agent, either the conjugate reduction products or the fully reduced products can be obtained in high selectivity. In contrast to analogous reactions catalyzed by air- and moisture-sensitive borane catalysts, the hemiboronic acid catalyzed protocol can be performed under ambient conditions. Profiling studies revealed that global reduction proceeds via a rapid initial 1,4-addition, followed by ketone deoxygenation with a rate that is highly silane-dependent.

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 score0.004
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)0.0010.000

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 head0.009
GPT teacher head0.226
Teacher spread0.217 · 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

Citations5
Published2023
Admission routes1
Has abstractyes

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