Exploiting Natural Complexity: Synthetic Terpenoid‐Alkaloids by Regioselective and Diastereoselective Hydroaminoalkylation Catalysis
Bibliographic record
Abstract
Abstract We report a catalytic and atom‐economic approach for the addition of N‐methyl groups to unactivated alkene‐containing terpenes to generate a library of synthetic terpenoid‐alkaloids. This catalysis was accomplished using Ta(CH 2 SiMe 3 ) 3 Cl 2 in combination with a new chiral ureate salt for highly chemo‐, regio‐, and diastereoselective hydroaminoalkylation reactions. The desired products are easily isolated and purified from unreacted starting materials to give aminated terpenes in one catalytic step. Starting material enantiopurity is completely retained, and stereoselective catalysis results to give enantiopure products. Absolute stereochemistry was determined by X‐ray crystallography and is consistent with regio‐ and stereoselective alkene insertion into a catalytically active tantallaziridine intermediate.
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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".