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C–N Ring Construction: The Waser Synthesis of Jerantinine E

2017· book-chapter· en· W3098027942 on OpenAlexaboutno aff
Douglass F. Taber

Bibliographic record

VenueOxford University Press eBooks · 2017
Typebook-chapter
Languageen
FieldChemistry
TopicSynthesis of β-Lactam Compounds
Canadian institutionsnot available
Fundersnot available
KeywordsChemistryAzetidineImineAziridineMedicinal chemistryRing (chemistry)StereochemistryCatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

James A. Bull of Imperial College London prepared (J. Org. Chem. 2013, 78, 6632) the aziridine 2 with high diastereocontrol by adding the anion of diiodomethane to the imine 1. Karl Anker Jørgensen of Aarhus University observed (Chem. Commun. 2013, 49, 6382) high ee in the distal aziridination of 3 to give 4. Benito Alcaide of the Universidad Complutense de Madrid and Pedro Almendros of ICOQ- CSIC Madrid reduced (Adv. Synth. Catal. 2013, 355, 2089) the β-lactam 5 to the azetidine 6. Hiroaki Sasai of Osaka University added (Org. Lett. 2013, 15, 4142) the allenoate 8 to the imine 7, delivering the azetidine 9 in high ee. Tamio Hayashi of Kyoto University, the National University of Singapore, and A*STAR devised (J. Am. Chem. Soc. 2013, 135, 10990) a Pd catalyst for the enanti­oselective addition of the areneboronic acid 11 to the pyrroline 10 to give 12. Ryan A. Brawn of Pfizer (Org. Lett. 2013, 15, 3424) reported related results. Nicolai Cramer of the Ecole Polytechnique Fédérale de Lausanne developed (J. Am. Chem. Soc. 2013, 135, 11772) a Ni catalyst for the cyclization of the formamide 13 to the lactam 14. Andrew D. Smith of the University of St. Andrews used (Org. Lett. 2013, 15, 3472) an organocatalyst to cyclize 15 to 16. Jose L. Vicario of the Universidad del Pais Vasco effected (Synthesis 2013, 45, 2669) the multicomponent coupling of 17, 18, and 19, mediated by an organocatalyst, to construct 20 in high ee. André Beauchemin of the University of Ottawa explored (J. Org. Chem. 2013, 78, 12735) the thermal cyclization of ω-alkenyl hydroxyl amines such as 21. Abigail G. Doyle of Princeton University developed (Angew. Chem. Int. Ed. 2013, 52, 9153) a Ni catalyst for the enantioselective addition of aryl zinc bromides such as 24 to the pro­chiral 23, to give 25 in high ee. Dennis G. Hall of the University of Alberta developed (Angew. Chem. Int. Ed. 2013, 52, 8069) an in situ preparation of the allyl boronate 26 in high ee. Addition to the aldehyde 27 proceeded with high diasteroselectivity.

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: Not applicable · Consensus signal: none
GenreCandidate signal: Methods · Consensus signal: none
Teacher disagreement score0.004
Threshold uncertainty score0.012

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 communication0.0000.001
Open science0.0010.001
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0040.002

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 head0.023
GPT teacher head0.200
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 source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designNot applicable
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".

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Citations0
Published2017
Admission routes1
Has abstractyes

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