Easy Routes towards Chiral Lithium Binaphthylamido Catalysts for the Asymmetric Hydroamination of Amino‐1,3‐dienes and Aminoalkenes
Bibliographic record
Abstract
Abstract The preparation of chiral lithium salts of N , N′ ‐disubstituted binaphthyldiamines and their use as catalysts for asymmetric hydroamination/cyclisation of amino‐1,3‐dienes and aminoalkenes are reported. Several straightforward methods involving the combination of ligand with solutions of methyl‐ or [(trimethylsilyl)methyl]lithium (LiCH 2 TMS) by ex situ or in situ preparation have been investigated. The use of LiCH 2 TMS in an in situ procedure was revealed as theeasiest for carrying out reactions with reliable results by fine‐tuning the quantity of base. Screening of a variety of ligands led to the selection of binaphthyldiamines modified by benzyl, pyridyl or naphthyl groups for the cyclisation of conjugated aminodienes in pyrrolidine or piperidine with the highest stereo‐ and enantioselectivities described to date (up to 61 and 72 % ee , respectively). Primary and secondaryaminoalkenes are efficiently cyclised at room temperature, but with poor enantioselectivities.
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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 | 0.001 | 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) | 0.000 | 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".