研究生: |
廖柏翔 Liao, Bo-Xiang |
---|---|
論文名稱: |
銠(I)金屬催化烯基硼酸試劑對α,β-不飽和酮類化合物的不對稱1,4-加成反應 Rhodium-Catalyzed Asymmetric 1,4-addition of Alkenylboronic acids to α,β-Unsaturated Carbonyl Compounds |
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: | 2014 |
畢業學年度: | 102 |
語文別: | 中文 |
論文頁數: | 182 |
中文關鍵詞: | 銠金屬 、烯基硼酸試劑 、α,β-不飽和酮類化合物 、不對稱1,4加成反應 、立體選擇性 、鏡像超越值 |
英文關鍵詞: | Rhodium, alkenylboronic acids, α,β-unsaturated carbonyl compounds, asymmetric conjugation addition, enantioselective, ee |
論文種類: | 學術論文 |
相關次數: | 點閱:210 下載:6 |
分享至: |
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
本論文是利用一價銠金屬和掌性樟腦型雙環[2.2.1]雙烯配基(25A)作為催化基,催化烯基硼酸試劑與α,β-不飽和酮類化合物進行不對稱1,4加成反應,利用各種不同的烯基硼酸試劑及α,β-不飽和酮類化合物合成出一系列β-烯基取代酮化合物。這些產物都具有很好的產率以及高的立體選擇性,產率最高可達99%,而鏡像超越值可高達>99.5% ee。
An efficient enantioselective conjugate addition of alkenylboronic acids to α,β-unsaturated carbonyl compounds was realized.
In the presence of 1 mol% of rhodium catalyst in situ prepared from [RhCl(C2H4)2]2 and ligand 25A, conjugation addition of various alkenylboronic acids to α,β-unsaturated carbonyl compounds furnishes the desired adducts in high yields (up to 99%) and in up to >99.5% ee.
參考文獻
1. Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
2. Kina, A.; Iwamura, H.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 3904.
3. Kina, A.; Yasuhara, Y.; Nishimura, T.; Iwamura, H.; Hayashi, T. Chem. Asian J. 2006, 1, 707.
4. Chen, F. X.; Kina, A.; Hayashi, T. Org. Lett. 2006, 8, 341.
5. Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852.
6. Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron:Asymmetry. 1999, 10, 4047.
7. (a) Brak, K.; Ellman, J. A. J. Org. Chem. 2010, 75, 3147. (b) Pucheault, M.; Darses, S.; Genet, J. P. Eur. J. Org. Chem. 2002, 3552.
8. (a) Pucheault, M.; Darses, S.; Genet, J. P. Tetrahedron Lett. 2002, 43, 6155. (b) Darses, S.; Genet, J. P. Eur. J. Org. Chem. 2003, 4313. (c) Molander, G. A.; Figueroa, R. Aldrichimica Acta. 2005, 38, 49.
9. Navarre, L.; Martinez, R.; Genet, J. P.; Darses, S. J. Am. Chem. Soc. 2008, 130, 6159.
10. (a) Batey, R. A.; Quach, T. D. Tetrahedron Lett. 2001, 42, 9099. (b) Molander, G. A.; Biolatto, B. Org. Lett. 2002, 4, 1867. (c) Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302. (d) Yuen, A. K. L.; Hutton, C. A. Tetrahedron Lett. 2005, 46, 7899. (e) Gendrineau, T.; Genet, J. -P.; Darses, S. Org. Lett. 2009, 11, 3486.
11. (a) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (b) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. Org. Synth. 2002, 79, 84.
12. (a) Yamamoto, Y.; Takizawa, M.; Yu, X.; Miyaura, N. Angew. Chem., Int. Ed. 2008, 47, 928. (b) Yu, X.; amamoto, Y.; Miyaura, N. Synlett 2009, 994.
13. Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2003, 68, 1901.
14. Shintani, R.; Tsutsumi, Y.; Nagaosa, M; Nishimura, T.; Hayashi, T. J. Am. Chem. Soc. 2009, 131, 13588.
15. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
16. (a) Itooka, R.; lguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. (b) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944.
17. Lukin, K.; Zhang, Q. Y.; Leanna, M. R. J. Org. Chem. 2009, 74, 929.
18. Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
19. Yamamoto, Y.; Kurihara, K.; Sugishita, N.; Oshita, K.; Piao, D. G.; Miyaura, N. Chem. Lett. 2005, 34, 1224.
20. Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508.
21. Defieber, C.; Paquin, J. –F.; Serna, S.; Carreira, E. M. Org. Lett. 2004, 6, 3873.
22. Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584.
23. Z. Q. Wang.; C. G. Feng.; S. S. Zhang.; M. H. Xu.; G. Q. Lin. Angew. Chem. Int. Ed. 2010, 49, 5780.
24. (a) Terada, M. J. Am. Chem. Soc. 2006, 128, 16044. (b) Connon, S. J. Angew. Chem. , Int. Ed. 2008, 47, 1176.
25. Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 38, 8479.
26. Otomaru, Y.; Hayashi, T. Tetrahedron: Asymmetry. 2004, 15, 2647.
27. Duursma, A.; Boiteau, J. G.; Lefort, L.; Boogers, J-A, F.; Vries, Andre´ H, M, de Vries.; Johannes G, de Vries.; Adriaan J, Minnaard.; Ben L, Feringa. J. Org. Chem. 2004, 69, 8045.
28. Stemmler, R, T.; Bolm, C. J. Org. Chem. 2005, 70, 9925.
29. Lalic, G.; Corey, E. J. Tetrahedron Lett. 2008, 49, 4894.
30. Shintani, R.; Ichikawa, Y.; Takatsu, K.; Fu-Xun, C.; Hayashi, T. J. Org. Chem. 2009, 74, 869.
31. Gendrineau, T.; Genet, J-P.; Darses, S. Org. Lett. 2009, 11, 3486.
32. Wang, Y.; Hu, X.; Du, H.; Org. Lett. 2010, 12, 5482.
33. Thaler, T.; Li-Na Guo.; Andreas K. Steib.; Raducan, M.; Karaghiosoff, K.; Mayer, P.; Knochel, P. Org. Lett. 2011, 13, 3182.
34. Trost, B. M.; Burns, A. C.; Tautz, T. Org. Lett. 2011, 13, 4566
35. Yu, H. J.; Shao, C.; Cui, Z.; Feng, C. G.; Lin, G. Q. Chem. Eur. J. 2012, 18, 13274.
36. Helbig, S.; Axenov, Kirill V.; Tussetschläger, S.; Frey, W.; Laschat, S. Tetrahedron Lett. 2012, 53, 3506.
37. Shirakawa, K.; Arase, A.; Hoshi, M. Synthesis. 2004, 11, 1814.
38. 國立臺灣師範大學 Syu, J. F. 畢業論文.