Diazepane Carboxylates as Organocatalysts in the Diels–Alder Reaction of α‐Substituted Enals
Bibliographic record
Abstract
Ethyl diazepane carboxylate efficiently catalyzes the Diels–Alder cycloaddition of α‐substituted‐α,β‐unsaturated aldehydes via iminium ion organocatalysis. The reaction is applicable to a range of dienes and dienophiles and generally proceeds at room temperature in the presence of 5 mol‐% catalyst and 2.5 mol‐% triflic acid co‐catalyst. The incorporation of a stereogenic center on the diazepane backbone in combination with a menthyl carbamate produces a catalyst which affords enantioselectivities of 70–95 % ee for the cycloaddition of cyclopentadiene with a range of dienophiles. The enantioselectivity is rationalized via a transition state in which electrostatic stabilization by the carboxylate directs the diene to the more hindered face of the dienophile.
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
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 | 0.001 | 0.001 |
| 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 | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.002 | 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".