Bisoxazoline–copper(I)-catalyzed aziridination of diazoacetate with imines — A DFT study
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Bibliographic record
Abstract
Density functional theory (DFT) has been used to study bisoxazoline–copper(I)-catalyzed aziridination of diazoacetate with syn-imines or anti-imines. All the intermediates and transition states were optimized completely at the B3LYP/6-31G(d) level. Calculation results confirm that Cu(I)-catalyzed aziridination goes mainly through the catalyst–diazoacetate complex (M1), the copper(I)–carbene intermediate (M2), the copper–carbene–imine complex (M3), and the catalyst–aziridine carboxylate complex (M4). For syn-imines, the reaction mode I (C3–N5 bond attacking the Cu–C1 bond of M2) is more dominant than the reaction mode II (C3–N5 bond attacking the carbene–carbon C1 of M2), and the attack from the si-surface of M2 is prior to the re-surface. For anti-imines, the reaction modes and attacks from the si- or re-surface coexist. The reactivity of syn-imines is stronger than anti-imines. The favorable reaction channel is CA2 → M1b → TS1b → M2 → syn-TS2b → syn-M3b → syn-TS3b → syn-M4b → syn-P2. The dominant product theoretically predicted is of (S,S)-chirality. On the whole, the solvent effect decreases the free energies of the species.
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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