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Record W2122645227 · doi:10.1039/b514952e

Making use of crystallization-induced asymmetric transformations in solid state organic photochemistry: application to the enantioselective Yang photocyclization of endo-bicyclo[2.1.1]hexyl aryl ketones

2005· article· en· W2122645227 on OpenAlexafffund
Wujiong Xia, John R. Scheffer, Brian O. Patrick

Bibliographic record

VenueCrystEngComm · 2005
Typearticle
Languageen
FieldChemistry
TopicMolecular spectroscopy and chirality
Canadian institutionsUniversity of British Columbia
FundersNatural Sciences and Engineering Research Council of CanadaCurtin University of Technology
KeywordsDiastereomerChemistryCrystallizationDiazomethaneArylBicyclic moleculeEnantioselective synthesisEnantiomerAmine gas treatingSalt (chemistry)Solid-stateMedicinal chemistryPhotochemistryStereochemistryOrganic chemistryAlkylPhysical chemistryCatalysis

Abstract

fetched live from OpenAlex

Achiral endo-bicyclo[2.1.1]hexyl aryl keto-acid 1a exists in solution as a rapidly equilibrating 1∶1 mixture of enantiomers. When a solution of this compound is treated with an optically pure amine, a crystallization-induced asymmetric transformation of the second kind takes place, and crystals of only one of the two possible diastereomeric salts are deposited. Irradiation of the crystals leads to a diastereoselective Yang photocyclization reaction of the carboxylate anion portion of the salt, and following diazomethane workup to form the corresponding methyl ester, high yields of novel cyclobutanols of structure 2 are formed in enantiomeric excesses as high as 90%.

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: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.001
Threshold uncertainty score0.002

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
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 head0.021
GPT teacher head0.288
Teacher spread0.267 · 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

Citations11
Published2005
Admission routes2
Has abstractyes

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