The Metal-Free, One-Pot Synthesis of Homoallylic Amines by Direct Alkylative Reductive Amination Using Allylsilatrane
Bibliographic record
Abstract
Homoallylic amines are versatile scaffolds that can give direct access to heterocycles such as azetidines, pyrrolidines, and quinolines. Existing approaches to synthesize homoallylic amines are typically inefficient, multi-step processes. They are commonly prepared through the allylation of pre-formed imines; such methods require inert conditions and use toxic tin reagents or use expensive titanium catalysts. We have developed a new metal-free, one-pot synthesis of homoallylic amines from aldehydes through direct alkylative reductive amination using 1-allylsilatrane, a bench-stable, easy-to-synthesize, hypercoordinate silane alkylating agent. This open-air reaction is completed in two hours at 40°C and gives good to excellent yields using various substituted anilines and aromatic aldehydes. We also demonstrate multiple utility pathways for homoallylic amines to be used as building blocks for biologically active molecules.
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 machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| 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) | 0.002 | 0.001 |
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 source (direct Gemma or distilled Codex), 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".