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Record W4235678797 · doi:10.1002/9783527809042.ch2

Benzoin Reaction

2018· other· en· W4235678797 on OpenAlexaff
Steven M. Langdon, Karnjit Parmar, Myron M. D. Wilde, Michel Gravel

Bibliographic record

Venuenot available
Typeother
Languageen
FieldChemistry
TopicN-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Canadian institutionsUniversity of Saskatchewan
Fundersnot available
KeywordsBenzoinChemistryCarbeneCatalysisElectrophileUmpolungEnantioselective synthesisAldimineReactivity (psychology)Organic chemistryImineMedicinal chemistryCombinatorial chemistryNucleophile

Abstract

fetched live from OpenAlex

In general, thiazolium and triazolium salts are used as precatalysts for N-heterocyclic carbene (NHC)-catalyzed benzoin reactions. Imidazolylidene catalysts are employed infrequently and are generally considered better suited for enolate/homo-enolate reactivity with enals. Aromatic aldehydes are generally well tolerated in the NHC-catalyzed homo-benzoin reaction. Aliphatic aldehydes and formaldehyde can be used in NHC-catalyzed homo-benzoin reactions, although they may require slightly modified reaction conditions. The triazolylidene NHC catalyst used in an enantioselective homo-benzoin reaction afforded improved yields and substantially improved enantioselectivity. Suzuki and coworkers reported the first intramolecular cross-benzoin reactions between aldehydes and ketones, using thiazolylidenes as catalysts in the synthesis of preanthraquinones. An aza-benzoin reaction arises when the electrophile in the carbon-carbon bond-forming step is replaced by an imine. Ketimines are much less reactive than aldimines, but they can nevertheless undergo aza-benzoin reactions, provided they bear additional electron-withdrawing substituents.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.016
Threshold uncertainty score0.053

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.001
Science and technology studies0.0010.000
Scholarly communication0.0010.001
Open science0.0000.001
Research integrity0.0010.002
Insufficient payload (model declined to judge)0.0160.008

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 head0.226
Teacher spread0.219 · 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 source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designNot applicable
Domainnot available
GenreOther

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

Citations2
Published2018
Admission routes1
Has abstractyes

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Same topicN-Heterocyclic Carbenes in Organic and Inorganic ChemistryFrench-language works237,207