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C–N Ring Construction: The Glorius Synthesis of ent-Monomorine

2017· book-chapter· en· W3105263978 on OpenAlexaboutno aff
Douglass F. Taber

Bibliographic record

VenueOxford University Press eBooks · 2017
Typebook-chapter
Languageen
FieldChemistry
TopicSynthesis and Catalytic Reactions
Canadian institutionsnot available
Fundersnot available
KeywordsEnantioselective synthesisChemistryImineElectrophilePyrroleStereochemistryCatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

Ryan Gilmour of the Westfälische Wilhelms-Universität Münster employed (Chem. Eur. J. 2014, 20, 794) an organocatalyst to direct the enantioselective aziridination of 1 to 2. Vanessa Kar-Yan Lo and Chi-Ming Che of Hong Kong University devised (Angew. Chem. Int. Ed. 2014, 53, 2982) a Ru catalyst for the enantioselective aziridi­nation (not illustrated) of terminal alkenes. Shu-Li You of the Shanghai Institute of Organic Chemistry and Aiwen Lei of Wuhan University described (Angew. Chem. Int. Ed. 2014, 53, 2443) the Pd-mediated carbonylation of 3 to the β-lactam 4. Professor You reported (J. Am. Chem. Soc. 2014, 136, 6590) the enantioselective allylation of a pyrrole 5 with 6 to give the imine 7. Maria-Paz Cabal and Carlos Valdés of the University of Oviedo showed (Eur. J. Org. Chem. 2014, 1672) that the cycliza­tion of 8 to 9 proceeded with predictable high diastereocontrol. In one pot, Darren J. Dixon of the University of Oxford combined (ACS Catal. 2014, 4, 634) 10 and 11 to give 12 in high ee. The addition of 13 to 14 to give 15 described (Nature Chem. 2014, 6, 47) by Takashi Ooi of Nagoya University set two adjacent quaternary centers with control of both relative and absolute configuration. Scott E. Denmark of the University of Illinois devised (J. Am. Chem. Soc. 2014, 136, 8915) a catalyst for the enantioselective electrophilic cyclization of 16 to 17 with control of sidechain stereochemistry. Using commercial acetone cyanohydrin 19, Christian V. Stevens of Ghent University cyclized (Eur. J. Org. Chem. 2014, 1296) 18 to the nitrile 20. George W. J. Fleet, also of the University of Oxford, used (Eur. J. Org. Chem. 2014, 2053) similar conditions to convert the sugar-derived acetonide 21 into 22. Michael B. Tropak of the University of Toronto and Dilip P. Dhavale of the University of Pune showed (J. Org. Chem. 2014, 79, 4398) that the nitrone derived from 21 added to an alkene 23 with high facial selectivity, leading to the piperidine 24. In the course of a synthesis of syringolin A, Satoshi Ichikawa of Hokkaido University effected (Angew. Chem. Int. Ed. 2014, 53, 4836) intramolecular Ugi three-component coupling of the isonitrile 25, the acid 26, and the amine 27, leading to the macrolactam 28.

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)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.982
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

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

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 head0.025
GPT teacher head0.201
Teacher spread0.177 · 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

Citations0
Published2017
Admission routes1
Has abstractyes

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