Migrative Reductive Amination of Ketones Enabled by Multitasking Reagents
Bibliographic record
Abstract
Secondary amines are key synthetic intermediates and constituents of pharmaceutical agents. They are often prepared by the classical reductive amination of ketones and aldehydes, a staple reaction in organic chemistry. Reductive amination forms products without modifying the carbon framework, which restricts its power and breadth. To expand chemical space and access isomeric amines with a rearranged skeleton, a migrative variant was developed by orchestrating three distinct reactions in a single flask, without solvent changes, using two inexpensive and nontoxic reagents: a Zn(II) salt and a hydrosilane. Mechanistic insights confirmed that both reagents are uniquely multitasking ─ active and synergistic ─ across all reaction stages, lending a practical open-flask procedure that embodies many ideals of green chemistry. This method demonstrates a wide scope of acyclic and cyclic ketones and aldehydes with both aliphatic and aromatic groups, including bioactive molecules and macrocyclic natural products isolated with highly favorable E-factor, process mass intensity, and other established greenness metrics. Furthermore, the efficiency of this migrative reductive amination was highlighted in a one-step synthesis of the marine natural product haliclorensin C from l-muscone.
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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 | 0.001 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 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".