研究生: |
丁奕晴 Ting, Yi-Ching |
---|---|
論文名稱: |
銠金屬(I)/掌性雙烯配體催化芳香基硼鹽對喹啉鹽進行不對稱芳基化反應 Enantioselective Rhodium-Catalyzed Arylation of Quinolinium Salts |
指導教授: |
吳學亮
Wu, Hsyueh-Liang |
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: | 284 |
中文關鍵詞: | 銠金屬 、掌性雙烯配體 、芳香基硼鹽 、喹啉鹽 、不對稱芳基化反應 |
英文關鍵詞: | Quinolinium Salts |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.070.2018.B05 |
論文種類: | 學術論文 |
相關次數: | 點閱:65 下載:0 |
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本論文是在探討以 3 mol %一價銠金屬及本實驗室所開發的雙環[2.2.1]樟腦型醯胺類雙烯配基 L7j 或雙環[2.2.1]樟腦型雙烯配基 L6i所形成的錯合物,以 1,4-二噁烷作為溶劑並在 100°C 下進行,催化一系列芳香基硼鹽對喹啉進行不對稱 1,2-加成反應,得到一系列以 氮-苄基-2-苯基-1,2-二氫喹啉化合物, 有高達 90%的產率以及 92%的鏡像超越值。
In this thesis, enantioselective arylation of N-Benzyl quinolinium salts is described. In the presence of 3 mol % ofthe catalyst generated in situ from [RhCl(C2H4)2]2 and chiral bicycloheptadiene ligand L7j or L6i, reaction of various quinolinium tetraarylborates gives rise to the corresponding enantio-enriched N-benzoy-2-aryl-1,2-dihydroquinolines in up to 90% yield with up to 92% ee at 100°C in dioxane.
1. Vellaisamy Sridharan; Padmakar A. Suryavanshi; J. Carlos Menéndez.Chem. Rev. 2011, 111, 7157–7259.
2. Keith M. Witherup; Richard W. Ransom; Amy C. Graham,AuroraM. Bernard; Michael J. Salvatore; William C. Lumma; Paul S.Anderson; Steven M. Pitzenberger; Sandor L. Varga. J. Am. Chem.Soc. 1995, 117, 6682-6685.
3. Jacquemond-Collet; Benoit-Vical F; Valentin A; Stanislas E; MalliéM; Fourasté. Planta Med. 2002, 1, 9.
4. Joseph P. Michael. Nat. Prod. Rep., 2001, 18, 543–559.
5. Bartholomeu A. Barros-Filho; Fátima M. Nunes; Maria C.F. deOliveira; Jair Mafezoli; Manoel Andrade-Neto; Edilberto R. Silveira;JoséR. Pirani. Biochemical Systematics and Ecology, 2004, 32, 817–821.
6. Fernando D. Suvire; Maximiliano Sortino; Vladimir V. Kouznetsov;Leonor Y. Vargas M; Susana A. Zacchino; Uriel Mora Cruzb; RicardoD. Enriza. Bioorg. Med. Chem. 2006, 14, 1851 –1862.
7. Atul R. Gholap; Kiran S. Toti; Fazal Shirazi; Ratna Kumari; ManojKumar Bhat; Mukund V. Deshpande; Kumar V. Srinivasana. Bioorg.Med. Chem. 2007, 15, 6705–6715.
8. Kirandeep Kaur; Meenakshi Jain; Ravi P. Reddy; Rahul Jain. Eur JMed Chem. 2010, 45, 3245–3264.
9. Charles Z. Ding, John T. Hunt, Carol Ricca, Veeraswamy Manne.Bioorg. Med. Chem. Lett. 2000, 10, 273–275.
10. Jing-Ping Liou, Zi-Yi Wu, Ching-Chuan Kuo, Chi-Yen Chang, Pei-YiLu, Chi-Ming Chen, Hsing-Pang Hsieh, Jang-Yang Chang. J. Med.Chem. 2008, 51, 4351 –4355.11. K. Nagaiah, A. Venkatesham, R. Srinivasa Rao, V. Saddanapu, J. S.Yadav, S. J. Basha, A. V. S. Sarma, B. Sridhar, A. Addlagatta. Bioorg.
Med. Chem. Lett. 2010, 20, 3259–3264.
12. Marion Raoul, Corinne Schaeffer, Stéphane Léonce, Alain Pierré,Ghanem Atassi, Reynald Hocquemillera, Guy Lewina. Bioorg. Med.Chem. Lett. 2001, 11, 79–81.
13. Michel C. Maillard, Michael E. Perlman, Oved Amitay, DeborahBaxter, David Berlove, Sonia Connaughton, James B. Fischer, JunQing Guo, Lain-Yen Hu, Robert N. McBurney, Peter I. Nagy,Katragadda Subbarao, Elizabeth A. Yost, Lu Zhang, Graham J. Durant.J. Med. Chem. 1998, 41, 3048-3061.
14. Shoji Fukumoto, Eiko Imamiya, Keiji Kusumoto, Shuji Fujiwara,Toshifumi Watanabe, and Mitsuru Shiraishi, J. Med. Chem. 2002, 45,3009-3021.
15. Vijay K. Gore, Vu V. Ma, Ruoyuan Yin, Joe Ligutti , David Immke ,Elizabeth M. Dohertya, Mark H. Norman , Bioorg. Med. Chem. Lett.2010, 20, 3573–3578.
16. Elizabeth M. Doherty, Christopher Fotsch, Yunxin Bo, Partha P.Chakrabarti, Ning Chen, Narender Gavva, Nianhe Han, MichaelG. Kelly, John Kincaid, Lana Klionsky, Qingyian Liu, Vassil I.Ognyanov, Rami Tamir, Xianghong Wang, Jiawang Zhu, Mark H.Norman, and James J. S. Treanor. J. Med. Chem. 2005, 48, 71 -90.17. Adam Banks, Gary F. Breen, Darren Caine, John S. Carey, ChristopherDrake, Michael A. Forth Asa Gladwin, Simone Guelfi, Jerome F.Hayes, Paolo Maragni, David O. Morgan, Paul Oxley, Alcide Perboni,Matthew E. Popkin, Fiona Rawlinson, Guillaume Roux. OrganicProcess Research & Development, 2009, 13, 1130–1140.
18. Jiwen Liu, Yingcai Wang, Ying Sun, Derek Marshall, Shichang Miao,George Tonn, Penny Anders,Joel Tocker, H. Lucy Tang, Julio Medina,Bioorg. Med. Chem. Lett. 2009, 19, 6840–6844.
19. Owen B. Wallace, Kenneth S. Lauwers, Scott A. Jones and Jeffrey A.Dodge, Bioorg. Med. Chem. Lett., 2003, 13, 1907–1910.
20. Margaret E. Brousseau, Ph.D., Ernst J. Schaefer, M.D., Megan L.Wolfe, B.S., LeAnne T. Bloedon, M.S., R.D., Andres G. Digenio,M.D., Ph.D., Ronald W. Clark, M.S., James P. Mancuso, Ph.D., DanielJ. Rader, M.D. N Engl J Med. 2004, 350, 1505-1515.
21. Gee-Hong Kuo, Thomas Rano, Patricia Pelton, Keith T. Demarest,Alan C. Gibbs, William V. Murray, Bruce P. Damiano, andMargery A.Connelly. Gee-Hong Kuo, Thomas Rano, Patricia Pelton, Keith T.Demarest, Alan C. Gibbs, William V. Murray, Bruce P. Damiano,Margery A. Connelly. J. Med. Chem. 2009, 52, 1768–1772.
22. Thomas A. Rano , Ellen Sieber-McMaster, Patricia D. Pelton, MariaYang, Keith T. Demarest, Gee-Hong Kuo. Bioorg. Med. Chem. Lett.,2009, 19, 2456–2460.23. Shigeki Hibi, Kouichi Kikuchi, Hiroyuki Yoshimura, Mitsuo Nagai,Kenji Tai, and Takayuki Hida. J. Med. Chem. 1998, 41, 3245-3252.
24. Cécile Parmenon a , Jérôme Guillard , Daniel-Henri Caignard ,Nathalie Hennuyer , Bart Staels , Valérie Audinot-Bouchez , JeanAlbert Boutin , Catherine Dacquet , Alain Ktorza , Marie-ClaudeViaud-Massuard, Bioorg. Med. Chem. Lett. 2009, 19, 2683–2687.
25. HyeSung Kim, HyoJin Gim, Mihi Yang, Jae-Ha Ryu, and Raok Jeon.HETEROCYCLES, Vol. 71, 10, 2007.
26. Howard C. Smith, Caitlin K. Cavanaugh, Jennifer L. Friz, Christine S.Thompson, Jessica A. Saggers, Enrique L. Michelotti, Javier Garciab,Colin M. Ticea. Bioorg. Med. Chem. Lett. 2003, 13, 1943–1946.
27. F Santangelo, C Casagrande, G Miragoli, V Vecchietti. Eur J MedChem, 1994, 29,877-882.
28. Lien Ai Nguyen, Hua He, Chuong Pham-Huy. Int J Biomed Sci. 2006,2, 85–100.
29. Ping Tian, Han-Qing Dong, Guo-Qiang Lin. ACS Catal. 2012, 2, 95−119.
30. De-Yang Zhang, Duo-Sheng Wang, Min-Can Wang, Chang-Bin Yu,Kai Gao, Yong-Gui Zhou. Synthesis, 2011, 17, 2796–2802.
31. Jialin Wen, Renchang Tan, Shaodong Liu, Qingyang Zhao, XumuZhang. Chem. Sci. 2016, 7, 3047–3051.
32. Christian Nadeau, Sara Aly, Kevin Belyk. J. Am. Chem. Soc. 2011,133, 2878–2880.
33. Yan Wang, Yunlong Liu, Dongdong Zhang, Hao Wei, Min Shi, Feijun Wang. Angew. Chem. Int. Ed. 2016, 55, 3776 –3780.34. Wei-Ting Wei, Jiann-Yih Yeh, Ting-Shen Kuo, Hsyueh-Liang Wu.
Chem. Eur. J. 2011, 17, 11405 – 11409.
35. Jin-Fong Syu, Huang-Ying Lin, Yu-Yi Cheng, Yao-Chu Tsai, Yi Ching Ting, Ting-Shen Kuo, Damodar Janmanchi, Ping-Yu Wu,
Julian P. Henschke, Hsyueh-Liang Wu. Chem. Eur. J. 2017, 23, 14515– 14522.
36. Dhananjayan Vasu, Hideki Yorimitsu, Atsuhiro Osuka. Angew. Chem.Int. Ed. 2015, 54, 7162 –7166.
37. Malcolm P. Roberts, Dolores Clavell-Grunbaum, Herbert L. Strauss.J. Chem. Phys. 1987, 87, 6393-6405.
38. Jixing Li, Jinlong Zhang, Huameng Yang, and Gaoxi Jiang. J. Org.Chem. 2017, 82, 3284 −3290.