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| 研究生： |
張富傑 Chang, Fu-Jie |
|---|---|
| 論文名稱： |
有機催化連鎖1,6/1,4/1,2/1,2-加成反應生成多取代之三環化合物 Diastereoselective Synthesis of Functionalized Angularly Fused Tricycles via an Organocascade Quadruple Reaction Involving Vinylogous 1,6/1,4/1,2/1,2-Addition Sequence |
| 指導教授： |
陳焜銘
Chen, Kwun-Min |
| 學位類別： |
碩士 Master |
| 系所名稱： |
化學系 Department of Chemistry |
| 論文出版年： | 2016 |
| 畢業學年度： | 104 |
| 語文別： | 中文 |
| 論文頁數： | 116 |
| 中文關鍵詞： | 有機連鎖反應 、1,6-加成反應 、三環 |
| 英文關鍵詞： | Organocascade, 1,6-addition, tricyclic |
| DOI URL： | https://doi.org/10.6345/NTNU202203973 |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：131 下載：0 |
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藉由三個分子化合物，進行有機連鎖四階反應，發展高非鏡像選擇性官能基的直並連三環化合物。使用1,3-茚二酮雙烯化合物與乙醯乙酸乙酯，利用20 mol%的硫尿素衍生之有機催化劑及加入20 mol%的1,4-二氮雜二環[2.2.2]辛烷，進行1,6/1,4/1,2/1,2-連鎖反應，得到密集官能基的三環化合物，有優異的產率（高達94%）及非鏡像選擇性（高達>20:1 dr）。此外，也經由單晶繞射X-ray確認其產物相對立體組態；然而，關於鏡像選擇性之有機連鎖反應仍在進行當中。
An efficient three components organocascade quadruple reaction has been developed and successfully accessed to the highly diastereoselective functionalized tricyclic compounds. The reaction between arylallylidene-indane-1,3diones and ethyl acetoacetate mediated by thiourea derived organocatalyst and DABCO via 1,6-/1,4-/1,2-/1,2-addition sequence to generate densely functionalized tricyclic outcomes with good yields (up to 94%) and excellent diastereoselectivities (up to >20:1 dr). The relatived configuration of the cyclized product was determined by the single crystal X-ray analysis. However, the enantiomeric version of the organocascade reaction is currently under investigation in our laboratory.
1. https://en.wikipedia.org/wiki/Organic_chemistry
2. https://en.wikipedia.org/wiki/Chirality
3. https://en.wikipedia.org/wiki/Thalidomide
4. Alemán, J.; Cabrera, S. Chem. Soc. Rev., 2013, 42, 774.
5. List, B.; Lerner, R. A.; Barbas, C. F. III. J. Am. Chem. Soc. 2000, 122, 2395.
6. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem Int. Ed. 2007, 46, 1570.
7. (a) List, B. Chem. Rev. 2007, 107, 5413. (b) Jacobsen, E. N.; Doyle, A. G. Chem. Rev. 2007, 107, 5713.
8. https://en.wikipedia.org/wiki/Quinine
9. Akiyama, T.; Itoh, J.; Yokota, K,; Fuchibe, K. Angew. Chem Int. Ed. 2004, 43, 1566.
10. Takemoto, Y.; Hoashi, Y.; Tomotaka, O. J. Am. Chem. Soc. 2003, 125, 12672.
11. Soós, T.; Vakulya, B.; Varga, S.; Csámpai, A. Org. Lett. 2005, 7, 1697.
12. Wang, W.; Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W. J. Am. Chem. Soc. 2007, 129, 1036.
13. Michael, A. J. Prakt. Chem. 1887, 35, 349.
14. Du, D. M.; Zhou, W. M.; Liu, H. Org. Lett. 2008, 10, 2817.
15. Pansare, S. V.; Pandya, K. J. Am. Chem. Soc. 2006, 128, 9624.
16. Melchiorre, P.; Silvi, M.; Chatterjee, I.; Liu, Y. Angew. Chem Int. Ed. 2013, 52, 10780.
17. Hayashi, Y.; Okamura, D.; Umemiya, S.; Uchimaru, T. ChemCatChem 2012, 4, 959.
18. Jørgensen, K. A.; Poulsen, P. H.; Feu, K. S.; Paz, B. M.; Jensen, F. Angew. Chem Int. Ed. 2015, 127, 8321.
19. Jørgensen, K. A.; Albrecht, L.; Jiang, H, Angew. Chem Int. Ed. 2011, 50, 8492.
20. Enders, D.; Hüttl, M. R.; Grondal, C.; Rabbe, G. Nature 2006, 441, 861.
21. Enders, D.; Blümel, M.; Chauhan, P.; Hahn, R.; Raabe, G. Org. Lett. 2014, 16, 6012.
22. Hong, B. C.; Kotame, P.; Liao, J. H. Tetrahedron Lett. 2009, 50, 704.
23. Hong, B. C.; Raja, A.; Lee, G. H. Org. Lett. 2014, 16, 5756.
24. (a) Pizzirani, D.; Roberti, M.; Grimaudo, S.; Cristina, A. D.; Pipitone, R. M.; Tolomeo, M.; Recanatini, M. J. J.Med. Chem. 2009, 52, 6936. (b) Nicolaou, K. C.; Montagnon, T.; Vassilikogiannakis, G.; Mathison, C. J. N. J. Am. Chem. Soc. 2005, 127, 8872.
25. Chen, K.; Chang, Y. P.; Gurubrahamam, R. Org. Lett. 2015, 17, 2908.
26. Inayama, S.; Mamoto, K.; Shibata, T.; Hirose, T. J. Med. Chem. 1976, 19, 433.
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