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New Methods for C-N Ring Construction

2011· book-chapter· en· W3099661330 on OpenAlexaboutno aff
Douglass Taber

Bibliographic record

VenueOxford University Press eBooks · 2011
Typebook-chapter
Languageen
FieldChemistry
TopicAsymmetric Hydrogenation and Catalysis
Canadian institutionsnot available
Fundersnot available
KeywordsHydroaminationIntramolecular forceRing (chemistry)IminePyrrolidineCatalysisChemistryMedicinal chemistryStereochemistryPolymer chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Chaozhong Li of the Shanghai Institute of Organic Chemistry demonstrated (Organic Lett. 2008, 10, 4037) facile and selective Cu-catalyzed β-lactam formation, converting 1 to 2. Paul Helquist of the University of Notre Dame devised (Organic Lett. 2008, 10, 3903) an effective catalyst for intramolecular alkyne hydroamination, converting 3 into the imine 4. Six-membered ring construction worked well also. Jon T. Njardarson of Cornell University found (Organic Lett. 2008, 10, 5023) a Cu catalyst for the rearrangement of alkenyl aziridines such as 5 to the pyrroline 6. Philippe Karoyan of the UPMC, Paris developed (J. Org. Chem. 2008, 73, 6706) an interesting chiral auxiliary directed cascade process, converting the simple precursor 7 into the complex pyrrolidine 9. Sherry R. Chemler of the State University of New York, Buffalo devised (J. Am. Chem. Soc. 2008, 130, 17638) a chiral Cu catalyst for the cyclization of 10, to give 12 with substantial enantiocontrol. Wei Wang of the University of New Mexico demonstrated (Chem. Commun. 2008, 5636) the organocatalyzed condensation of 13 and 14 to give 16 with high enantio- and diastereocontrol. Two complementary routes to azepines/azepinones have appeared. F. Dean Toste of the University of California, Berkeley showed (J. Am. Chem. Soc. 2008, 130, 9244) that a gold complex catalyzed the condensation of 17 and 18 to give 19. Frederick G. West of the University of Alberta found (Organic Lett. 2008, 10, 3985) that lactams such as 20 could be ring-expanded by the addition of the propiolate anion 21. Takeo Kawabata of Kyoto University extended (Organic Lett . 2008, 10, 3883) “memory of chirality” studies to the cyclization of 23, demonstrating that 24 was formed in high ee. Paul V. Murphy of University College Dublin took advantage (Organic Lett . 2008, 10, 3777) of the well-known intramolecular addition of azides to alkenes, showing that the intermediate could be intercepted with nucleophiles such as thiophenol, to give the cyclized product 26 with high diastereocontrol.

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)0.001
metaresearch head score (Gemma)0.001
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: Methods · Consensus signal: Methods
Teacher disagreement score0.009
Threshold uncertainty score0.031

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.001
Bibliometrics0.0010.001
Science and technology studies0.0010.001
Scholarly communication0.0010.002
Open science0.0010.002
Research integrity0.0010.002
Insufficient payload (model declined to judge)0.0090.005

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 head0.036
GPT teacher head0.252
Teacher spread0.216 · 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
GenreMethods

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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