Efficient Preparation of the Isoindoline Framework <i>via</i> a Six Component, Tandem Double A<sup>3</sup>‐Coupling and [2+2+2] Cycloaddition Reaction
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Bibliographic record
Abstract
Abstract The preparation of tetrasubstituted isoindolines from three alkyne units, two aldehyde units and a primary amine via three consecutive reactions, two aldehyde‐amine‐alkyne couplings (A 3 ‐couplings) and a final [2+2+2] cycloaddition, in a single synthetic operation, is described. The A 3 ‐couplings are catalyzed by copper bromide and the cycloaddition is catalyzed by Wilkinson’s catalyst. It was found that many catalysts known to be efficient at the cycloaddition step were not suitable when this step was part of the tandem reaction sequence. Wilkinson’s catalyst was found to be unique in its suitability for the overall domino reaction sequence.
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Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.001 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it