Remote Asymmetric Induction via a Chiral Acetylene Equivalent
Bibliographic record
Abstract
Asymmetric transformations have, to date, typically relied on proximal steric biasing to favor the formation of one enantiomer over the other during the enantiodetermining step. We report the use of an enantioenriched oxabicycle that serves both as a chiral auxiliary and an acetylene surrogate following two selective palladium-catalyzed carbopalladations and a postcatalytic retro-Diels–Alder step. Differentiating functional groups, that are remote from the reactive alkene, direct the reaction with an ortho -iodostyrene and a terminating reagent in a domino fashion, providing enantioenriched indenes. The phosphine ligand has a dramatic influence on the overall process, as alkyl- and arylphosphines lead to opposite major enantiomers of the final indene product.
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How this classification was reachedexpand
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) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 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 itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
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".