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Record W2951502661 · doi:10.1021/bk-2005-0911.ch016

Polyfluorinated Binaphthol Ligands in Asymmetric Catalysis

2005· book-chapter· en· W2951502661 on OpenAlexaff
Yu Chen, Andrei K. Yudin

Bibliographic record

VenueACS symposium series · 2005
Typebook-chapter
Languageen
FieldChemistry
TopicAxial and Atropisomeric Chirality Synthesis
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsEnantioselective synthesisSteric effectsDiethylzincChemistryCatalysisCombinatorial chemistryChirality (physics)AlkylationStereochemistryOrganic chemistryPhysics

Abstract

fetched live from OpenAlex

Introduction Modern asymmetric synthesis relies on new and improved catalytic transformations. Understanding the balance of steric and electronic factors is a prerequisite to fine-tuning a catalyst to achieve optimal selectivity in a particular reaction. Among the chiral ligands developed so far, BINOL 1 and related molecules with axial chirality have found wide utility in asymmetric catalysis (1). 1BINOL BINOL was first synthesized in 1926 (2), however, its potential as a ligand for metal-mediated catalysis was left unrecognized until 1979 when Noyori demonstrated its utility in the reduction of aromatic ketones and aldehydes (3). Since Noyori's discovery, many modifications of the BINOL skeleton aimed at changing its steric and electronic properties have been reported (4). For example, partially hydrogenated BINOL was used in enantioselective alkylation of aldehydes (4a); conjugate addition of diethylzinc to cyclic enones (4b); and ring opening of epoxides (4c). Selective bromination at the 6 and 6' positions of the

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: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.723
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0010.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0010.001
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 head0.206
Teacher spread0.197 · 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 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

Citations1
Published2005
Admission routes1
Has abstractyes

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