Origins and applications of stereoselective sulfenate anion alkylation reactions
Why this work is in the frame
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Bibliographic record
Abstract
Selected sulfenate anions can be alkylated with diastereoselectivities near 9:1 when there is appropriately positioned carbon chirality in the sulfenate structure or in the alkylation electrophile. Both protocols represent a conceptually different approach to β-amino sulfoxides. When vinylic β-amino sulfoxides are cyclized, thiomorpholine S-oxides result, and substrate control over the stereochemistry of alkyl substituents was found. This finding facilitates the synthesis of cis and trans dialkylpyrrolidines, known ant venom alkaloids. A computational model is demonstrated to account for some of the diastereoselection results. The importance of intramolecular interactions of sulfenate constituent atoms with pendent substituents is established.
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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) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| 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 it