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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 ). 1 1. BINOL High Resolution Image Download MS PowerPoint Slide 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 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: Bench or experimental · Consensus signal: none
GenreCandidate signal: Empirical · Consensus signal: none
Teacher disagreement score0.011
Threshold uncertainty score0.035

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 studies0.0000.000
Scholarly communication0.0010.001
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0110.005

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 source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
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

Citations1
Published2005
Admission routes1
Has abstractyes

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