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Transition Metal-Mediated C-C Ring Construction: The Stoltz Synthesis of (-)-Cyanthiwigin F

2011· book-chapter· en· W3102013609 on OpenAlexaboutno aff
Douglass Taber

Bibliographic record

VenueOxford University Press eBooks · 2011
Typebook-chapter
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsnot available
Fundersnot available
KeywordsCyclopropanationIntramolecular forceCyclopropaneChemistryTransition metalStereochemistryMethyleneChirality (physics)CatalysisEnantioselective synthesisAlkeneRing (chemistry)Medicinal chemistryPhysicsOrganic chemistry

Abstract

fetched live from OpenAlex

X. Peter Zhang of the University of South Florida extended (Organic Lett. 2009, 11, 2273) Co-catalyzed asymmetric cyclopropanation to the activated ester 2. The product 3 readily coupled with amines. André B. Charette of the Université de Montréal showed (J. Am. Chem. Soc. 2009, 131, 6970) that even α-olefins such as 4 could be cyclopropanated in high ee with the diazo amide 5. Xue-Long Hou of the Shanghai Institute of Organic Chemistry established (J. Am. Chem. Soc. 2009, 131, 8734) conditions for the enantioselective coupling of 7 and 8 to give 9 , in which sidechain chirality was also controlled. Tristan H. Lambert of Columbia University found (J. Am. Chem. Soc. 2009, 131, 7536) that “methylene” could be transferred in an intramolecular sense from the epoxide of 10 to the alkene, delivering the cyclopropane 11 in high ee. Yuichi Kobayashi of the Tokyo Institute of Technology established (Organic Lett . 2009, 11, 1103) that the 2-picolinoxy leaving group worked well for the SN2' coupling with 13 to give 14. Chang Ho Oh of Hanyang University developed (J. Org. Chem. 2009, 74, 370) a new route to cyclopentenones such as 16, by gold-catalyzed cyclization of diynes such as 15. David J. Procter of the University of Manchester used (J. Am. Chem. Soc. 2009, 131, 7214; Tetrahedron Lett . 2009, 50, 3224) SmI2 to cyclize 17 to 18 and 19 to 20, each with high diastereocontrol. Yoshiaki Nishibayashi of the University of Tokyo devised (Angew. Chem. Int. Ed. 2009, 48, 2534) Ru catalysts for the cyclization of an enyne such as 21 to the cyclohexadiene 22. Laurel L. Schafer of the University of British Columbia developed (J. Am. Chem. Soc. 2009, 131, 2116) a Zr catalyst for the diastereocontrolled cyclization of amino alkenes such as 23. Hongbin Zhai of the Shangahi Institute of Organic Chemistry showed (J. Org. Chem. 2009, 74, 2592) that the Mo-mediated cyclization of 25 also proceeded with high diastereocontrol. Even more impressive was the selectivity Kozo Shishido of the University of Tokushima demonstrated (Tetrahedron Lett . 2009, 50, 1279) for the cyclization of 27.

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: Theoretical or conceptual · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.907
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 studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
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 head0.021
GPT teacher head0.180
Teacher spread0.159 · 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 designTheoretical or conceptual
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
Published2011
Admission routes1
Has abstractyes

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