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Transition Metal-Catalyzed Reactions of 3-Aza-2-oxabicyclo[2.2.1]hept-5-enes

2018· article· en· W2803972408 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueCurrent Organic Synthesis · 2018
Typearticle
Languageen
FieldChemistry
TopicClick Chemistry and Applications
Canadian institutionsUniversity of Guelph
Fundersnot available
KeywordsChemistryAlkeneTransition metalCatalysisBond cleavageStereoselectivityCleavage (geology)Organic synthesisCombinatorial chemistryMetalOrganic reactionTransition stateOrganic chemistryStereochemistry

Abstract

fetched live from OpenAlex

Background: Transition metal catalysts are becoming increasingly more important in organic synthesis and are being used to catalyze novel reactions that allow for more efficient synthesis of many pharmaceuticals. Transition metal-catalyzed reactions of 3-aza-2-oxabicyco[2.2.1]hept-5-enes provide efficient synthetic pathways to generate a diverse range of biologically and synthetically useful products. 3-Aza-2- oxabicyclic alkenes undergo three main types of reactions: reductive N-O bond cleavage, C-O bond cleavage, and modification of the alkene component. Objective: The purpose of this review is to summarize and discuss the transition metal-mediated reactions of 3- aza-2-oxabicyclo[2.2.1]hept-5-enes, including the mechanisms of reactions based on the transition metal used, the different stereo- and regiochemical outcomes of reactions with this asymmetrical substrate, and the biological importance of exploring these reactions. Conclusion: It is clear from the review of the topic that a vast amount of work has been done in this area, and transition metals have been used to control the regio- and stereoselective reactions of 3-aza-2-oxabicyclic alkenes to create biologically active and synthetically useful products. The transition metal-catalyzed reactions of 3-aza-2-oxabicyclic alkenes proceed through three general reactions: through cleavage of the N-O bond, cleavage of the C-O bond, and modification of the alkene component. Without the use of transition metals, the substrate would not be activated and these reactions would not be possible. The use of transition metals opens up an array of new reactions that have the ability to create different functional groups with different regio- and stereoselectivities based on the metal and conditions used. The products made through these transition metalcatalyzed reactions can be useful as antibiotics, siderophores, and carbocyclic nucleosides such as noraristeromycin and carbocyclic polyoxin C.

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.

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 categoriesInsufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.023
Threshold uncertainty score0.991

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 integrity0.0000.000
Insufficient payload (model declined to judge)0.0100.000

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 head0.028
GPT teacher head0.277
Teacher spread0.249 · 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