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C-N Ring Construction: The Zakarian Synthesis of (-)-Rhazinilam

2013· book-chapter· en· W3101043770 on OpenAlexaboutno aff
Douglass F. Taber

Bibliographic record

VenueOxford University Press eBooks · 2013
Typebook-chapter
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicAlkaloids: synthesis and pharmacology
Canadian institutionsnot available
Fundersnot available
KeywordsEnantiomerAziridineImineChemistryEnantioselective synthesisMalonateStereochemistryRing (chemistry)CatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

William D. Wulff of Michigan State University developed (J. Am. Chem. Soc. 2010, 132, 13100; Org. Lett. 2010, 12, 4908) a general enantio- and diastereocontrolled route from an imine 1 to the aziridine 3. Craig W. Lindsley of Vanderbilt University established (Org. Lett. 2010, 12, 3276) a complementary approach (not illustrated). Joseph P. Konopelski of the University of California, Santa Cruz, designed (J. Am. Chem. Soc. 2010, 132, 11379) a practical and inexpensive flow apparatus for the cyclization of 4 to the β-lactam 5. Manas K. Ghorai of the Indian Institute of Technology, Kanpur, showed (J. Org. Chem. 2010, 75, 6173) that an aziridine 6 could be opened with malonate to give the γ-lactam 8. John P. Wolfe of the University of Michigan devised (J. Am. Chem. Soc. 2010, 132, 12157) a Pd catalyst for the enantioselective cyclization of 9 to 11. Sherry R. Chemler of the State University of New York at Buffalo observed (Angew. Chem. Int. Ed. 2010, 49, 6365) that the cyclization of 12 to 14 proceeded with high diastereoselectivity. Glenn M. Sammis of the University of British Columbia devised (Synlett 2010, 3035) conditions for the radical cyclization of 15 to 16. Jeffrey S. Johnson of the University of North Carolina observed (J. Am. Chem. Soc. 2010, 132, 9688) that the opening of racemic 17 with 18 could be effected with high ee. The residual 17 was highly enriched in the nonreactive enantiomer. Kevin D. Moeller of Washington University found (Org. Lett . 2010, 12, 5174) that the n -BuLi catalyzed cyclization of 20 set the quaternary center of 21 with high relative control. Yujiro Hayashi of the Tokyo University of Science, using the diphenyl prolinol TMS ether that he developed as an organocatalyst, designed (Org. Lett. 2010, 12, 4588) the sequential four-component coupling of 22, 23, benzaldehyde imine, and allyl silane to give 24 with high relative and absolute stereocontrol. Derrick L. J. Clive of the University of Alberta showed (J. Org. Chem. 2010, 75, 5223) that 25, prepared in enantiomerically pure form from serine, participated smoothly in the Claisen rearrangement, to deliver 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), Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.974
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0010.001
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0010.002
Insufficient payload (model declined to judge)0.0050.000

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 head0.084
GPT teacher head0.312
Teacher spread0.228 · 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
Published2013
Admission routes1
Has abstractyes

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