Transition-Metal Catalyzed Ring Construction: The Yu Synthesis of α-Agorafuran
Bibliographic record
Abstract
Valery V. Fokin of Scripps/La Jolla extended (J. Am. Chem. Soc. 2010, 132, 2510) enantioselective Rh-mediated intermolecular cyclopropanation to α-olefins such as 1. Takahiro Nishimura and Tamio Hayashi of Kyoto University developed (Angew. Chem. Int. Ed. 2010, 49, 1638) a procedure for enantioselective intramolecular cyclopropanation, beginning with a propargyl sulfonamide 4. Gerhard Hilt of Philipps-Universität Marburg established (Organic Lett. 2010, 12, 1536) that an aryl alkyne 6 could add to cyclopentene to give the cyclobutene 7. Hajime Ito of Hokkaido University devised (J. Am. Chem. Soc. 2010, 132, 5990) a protocol for the borylation of an alkenyl silane 8 to give an intermediate α-lithio silane, which cyclized to the cyclobutane 9 with high diastereoconrol. Aryl alkenes worked as well. This same approach could be used to construct cyclopentanes and cyclohexanes. Zhi-Xiang Yu of Peking University showed (J. Am. Chem. Soc. 2010, 132, 4542) that the triene 10 cyclized to the cyclopentane 11 with high diastereocontrol. Yong Tang of the Shanghai Institute of Organic Chemistry optimized (Angew. Chem. Int. Ed. 2010, 49, 4463) a Cu catalyst for the enantioselective Nazarov cyclization of 12 to 13. The meso bis-carbonates 14 and 16 were prepared by singlet oxygenation of the inexpensive cyclopentadiene. Mark Lautens of the University of Toronto developed (J. Org. Chem. 2010, 75, 4056) a protocol for the enantioselective coupling of 14 to an arene boronic acid, giving the carbonate 15 with high enantiocontrol. Professor Ito devised (Angew. Chem. Int. Ed. 2010, 49, 560) a complementary procedure, coupling 16 with bis-pinacolatoborane to give an intermediate allylborinate, that then added to the aldehyde 18 to give 19 with high stereocontrol. It would be interesting to know if these procedures worked as well with the meso bis-carbonates derived from cyclohexadiene. Saim Özkar of Middle East Technical University prepared (J. Am. Chem. Soc. 2010, 132, 6541) Ru nanoclusters stabilized by a zeolite framework that effected hydrogenation of 20 at near ambient conditions, in contrast to the high pressure and temperature usually required.
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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 | 0.000 | 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 | 0.001 | 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 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".