Catalysis of the Hajos—Parrish—Eder—Sauer—Wiechert Reaction by <i>cis</i>‐ and <i>trans</i>‐4,5‐Methanoprolines: Sensitivity of Proline Catalysis to Pyrrolidine Ring Conformation
Why this work is in the frame
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Bibliographic record
Abstract
Abstract Methanoprolines are found to be catalysts for the Hajos–Parrish–Eder–Sauer–Wiechert reaction. [1] cis ‐4,5‐Methanoproline exhibits catalytic ability similar to proline (86% yield, 93% ee ), whereas the trans ‐4,5‐methanoproline is less selective (67% yield, 83% ee ) and shows less acceleration. The reaction was also studied with hybrid density functional theory (B3LYP). The nearly planar cis ‐4,5‐methanoproline amine better reflects the planar iminium of the transition states than the pyramidalized trans ‐4,5‐methanoproline. This difference in conformation is responsible for the observed higher enantioselectivity and enhanced catalytic behavior of the cis ‐4,5‐methanoproline.
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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 | 0.002 | 0.002 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.002 | 0.001 |
| Bibliometrics | 0.001 | 0.003 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 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