研究生: |
余純瑋 Yu, Chun-Wei |
---|---|
論文名稱: |
鏡像選擇合成呋喃[2,3-b]呋喃結構經由Michael/縮醛化/縮醛化連鎖反應 Enantioselective Synthesis of Furo[2,3-b]furan Scaffolds via Michael/Acetalization/Acetalization Cascade Reaction |
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: | 2018 |
畢業學年度: | 106 |
語文別: | 中文 |
論文頁數: | 131 |
中文關鍵詞: | Michael反應 、有機連鎖反應 、縮醛化 、六環 、呋喃[2,3-b]呋喃 |
英文關鍵詞: | Michael reaction, Organocascade, Acetalization, hexacyclic, Furo[2,3-b]furan |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.028.2018.B05 |
論文種類: | 學術論文 |
相關次數: | 點閱:109 下載:0 |
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本實驗室成功利用Michael/縮醛化/縮醛化連鎖反應,使用低毒性溶劑及溫和反應條件,建構出連續六環呋喃[2,3-b]呋喃結構衍生物,有四個立體中心,具有適中的產率及良好至優異的鏡像超越值。反應以1,3-茚二酮衍生物(1.5 equiv.)及β-四氫萘酮(1.0 equiv.)於甲苯溶劑下,使用奎寧衍生之方烯胺有機掌性氫鍵催化劑(20 mol%),反應4小時後,可得到連續六環呋喃[2,3-b]呋喃結構衍生物,產率最高可達86%,鏡像超越值最高可達97%ee,經由再結晶純化可達> 99.5% ee。更多相關研究於本實驗室進行中。
Our lab successfully synthesized continuous hexacyclic furo[2,3-b]furan scaffold derivatives with four stereogenic centers via Michael/acetalization/acetalization cascade reations. Reaction starting materials were 1,3-indanedion derivatives (1.5 equiv.) and β-tetralone(1.0 equiv.) which were stirred in toluene and used quinine derived squaramide as hydrogen bond organocatalyst. After reaction lasting for 4 hours, continuous hexacyclic furo[2,3-b]furan scaffold derivatives formed with up to 86% yield and up to 97% ee . The enantiomeric excess could be enhanced to over 99.5% ee by recrystalization. The absolute configurations of the cyclized product was determined by the single crystal X-ray analysis. Further related researches are underway in our lab.
1. https://zh.wikipedia.org/wiki/%E6%9F%A0%E7%83%AF
2. 顧祐瑞(2007):藥學的第一堂課。臺北市:五南圖書出版股份有限公司。
3. https://scitechvista.nat.gov.tw/c/sKEp.htm
4. List, B.; Lerner, R. A.; Barbas III, C. F. J. Am. Chem. Soc. 2000, 122, 2395.
5. Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
6. Akiyama, T.; Itoh, J.; Yokota, K,; Fuchibe, K. Angew. Chem Int. Ed. 2004, 43, 1566.
7. Sigman, M. S.;Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
8. Takemoto, Y.; Hoashi, Y.; Tomotaka, O. J. Am. Chem. Soc. 2003, 125, 12672.
9. Soós, T.; Vakulya, B.; Varga, S.; Csámpai, A. Org. Lett. 2005, 7, 1967.
10. Robinson, R. J. Chem. Soc. 1917, 111, 762.
11. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem. Int. Ed. 2006, 45, 7134.
12. Pellissier, H. Adv. Synth. Catal. 2012, 354, 237.
13. Yang, J. W.; Fonseca, M. T. H.; List, B. J. Am. Chem. Soc. 2005, 127, 15036.
14. Marigo, M.; Schulte, T.; Franzén, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710.
15. Michael, A. J. Prakt. Chem. 1887, 35, 349.
16. https://en.wikipedia.org/wiki/Acetal
17. Kim, J. H.; Čorić, I.; Vellalath, S.; List, B. Angew. Chem. Int. Ed. 2013, 52, 4474.
18. Uchiyama, M.; Hirai, M.; Nagata, M.; Katoh, R.; Ogawa, R.; Ohta, A. Tetrahedron Letters. 2001, 42, 4653.
19. Alonso, F.; Sánchez, D.; Soler, T.; Yusa, M. Adv. Synth. Catal. 2008, 350, 2118.
20. Rashid, S.; Bhat, B. A.; Mehta, G. Org. Lett. 2015, 17, 3604.
21. Weisser, R.; Yue, W.; Reiser, O. Org. Lett. 2005, 7, 5353.
22. Brunetière, A.P.; Lallemand, J. Y. Tetrahedron Letters. 1988, 29, 2179.
23. Vader, J.; Sengers, H.; de Groot, A. Tetrahedron. 1989, 45, 2131.
24. Lee, C.-J.; Sheu, C.-N.; Tsai, C.-C.; Wu, Z.-Z.; Lin, W. Chem. Commun. 2014, 50, 5304.
25. Yang, S.-M.; Reddy, G. M.; Wang, T.-P.; Yeh, S.-Y.; Wang, M.; Lin, W. Chem. Commun. 2017, 53, 7649.
26. Chen, J.-H.; Chang, C.; Chang, H.-J.; Chen, K. Org. Biomol. Chem. 2011, 9, 7510.