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Record W3139319078 · doi:10.1002/adsc.202001472

Practical Stereoselective Synthesis of C3‐Spirooxindole‐ and C2‐Spiropseudoindoxyl‐Pyrrolidines <i>via</i> Organocatalyzed Pictet‐Spengler Reaction/Oxidative Rearrangement Sequence

2021· article· en· W3139319078 on OpenAlex
Masaru Kondo, Naoki Matsuyama, Tin Zar Aye, Irshad Mattan, Tomoyuki Sato, Yoshinori Makita, Masami Ishibashi, Midori A. Arai, Shinobu Takizawa, Hiroaki Sasai

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

VenueAdvanced Synthesis & Catalysis · 2021
Typearticle
Languageen
FieldChemistry
TopicAsymmetric Synthesis and Catalysis
Canadian institutionsArtificial Intelligence in Medicine (Canada)
FundersResearch Foundation for Opto-Science and TechnologyIketani Science and Technology Foundation
KeywordsChemistryTryptaminesStereoselectivityEnantioselective synthesisPictet–Spengler reactionCombinatorial chemistryOrganocatalysisOrganic chemistryStereochemistryCatalysisTryptamine

Abstract

fetched live from OpenAlex

Abstract A stereoselective synthetic route to chiral C3‐spirooxindole‐ and C2‐spiropseudoindoxyl‐pyrrolidines was accomplished by an enantioselective organocatalyzed Pictet‐Spengler reaction of tryptamines and isotryptamines followed by a diastereoselective oxidative rearrangement using eco‐friendly oxidants (i. e., NaOCl ⋅ 5H 2 O and Oxone®). This sequential reaction enables rapid access to chiral C3‐spirooxindole‐ and C2‐spiropseudoindoxyl‐pyrrolidines in a one‐pot process. A Wnt signaling inhibitory assay of the prepared enantioenriched spiro compounds demonstrated that they exhibited moderate activities. magnified image

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)0.001
metaresearch head score (Gemma)0.007
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
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 score0.258
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.007
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0000.002
Science and technology studies0.0000.000
Scholarly communication0.0000.001
Open science0.0010.000
Research integrity0.0000.000
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 head0.275
Teacher spread0.254 · 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