Iodine(III)-mediated synthesis of chiral α-substituted ketones: recent advances and mechanistic insights
Why this work is in the frame
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Bibliographic record
Abstract
Abstract The development of iodine(III)-mediated synthetic transformations has received growing interest, in particular to mediate enantioselective processes. In this class, the α-tosyloxylation of ketone derivatives using iodine(III) is a particularly powerful one, as it yields α-tosyloxy ketones – versatile chiral precursors that enable rapid access to numerous α-chiral ketones through nucleophilic displacement. Despite years of research from numerous groups, the enantioselectivities for this transformation have remained modest. Using quantum chemical calculations, we have uncovered a possible rational for the lack of selectivity. With these computational insights, we have developed an alternative experimental strategy and achieved unprecedented levels of selectivities. Applying this newfound knowledge, we have recently developed a new method to access α-halo ketones from non-ketonic precursors.
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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) | 0.001 | 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