(Methylcarboxymethylene)tripropylphosphorane: A Stabilized Ylide for Rapid Formation of Methyl Vinyl Ketones and Applications in Medicinal Chemistry and Natural Product Synthesis
Bibliographic record
Abstract
Abstract The synthesis of (methylcarboxymethylene)tripropylphosphorane, a new air-, water- and light-stable phosphonium ylide for the rapid formation of methyl vinyl ketones from various aldehyde starting materials is reported. This stabilized ylide provides high reaction yields and an excellent degree of E/Z stereoselectivity (>20:1). Furthermore, removal of phosphine oxide is accomplished during aqueous work-up, thus bypassing the need for column chromatography. The versatility of this ylide is demonstrated by the synthesis of methyl vinyl ketones from aryl as well as sensitive enolizable and functionalized aliphatic aldehydes, along with applications of these in the synthesis of olivetol, olivetolic acid, hygroline, and hygrine.
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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 | 0.000 |
| 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 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".