Studies on enolate chemistry of 8-thiabicyclo[3.2.1]- octan-3-one: enantioselective deprotonation and synthesis of sulfur analogs of tropane alkaloids
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Bibliographic record
Abstract
Enantioselective deprotonation of 8-thiabicyclo[3.2.1]octan-3-one (1) with chiral lithium amides, followed by reactions with electrophiles affords sulfur analogs of tropane alkaloids of pyranotropane family. Thus, deprotonation of 1 with (S)-N-(diphenyl)methyl-1-phenylethylamine (11d), followed by the reaction of the resulting nonracemic enolate with benzaldehyde gives the corresponding aldol product as one diastereoisomer (exo, threo) and in high enanatiomeric purity (95% ee). Trimethylsilyl chloride, acetic anhydride, and acyl cyanides react readily with the lithium enolate to give the corresponding derivatives of 1, however common alkylating agents fail to provide C-alkylated products. The reaction with acyl cyanides derived from α,β-unsaturated carboxylic acids (e.g., cinnamoyl cyanide) can be utilized in synthesis of thia-analogs of tropane alkaloids physoperuvine and isobellendine (13, 15).Key words: enantioselective deprotonation, tropane alkaloids.
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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 | 0.003 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| 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