研究生: |
楊舒涵 |
---|---|
論文名稱: |
高鏡像選擇性銠(I)/掌性雙烯配體催化芳香基硼酸對馬來醯亞胺進行不對稱1,4加成反應及其合成應用α2腎上腺素受體拮抗劑全合成及合成掌性HSD-1的抑制劑前驅物 |
指導教授: | 吳學亮 |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2013 |
畢業學年度: | 101 |
語文別: | 中文 |
論文頁數: | 284 |
中文關鍵詞: | 馬來醯亞胺 、不對稱共軛加成 、銠金屬 |
英文關鍵詞: | asymmetric addition, maleimide, Rh(I) |
論文種類: | 學術論文 |
相關次數: | 點閱:200 下載:0 |
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本論文敘述以一價銠金屬與掌性雙烯配體形成之催化劑催化不對稱芳香基硼酸加成至馬來醯亞胺 (maleimides) 加成來合成出一系列具有不對稱中心的3-芳香基取代的琥珀醯亞胺 (3-Aryl Succinimide) 化合物。
以一價銠金屬及掌性雙烯配體77b所形成之錯合物催化馬來醯亞胺 (maleimides) 化合物與各種芳香基硼酸試劑進行不對稱共軛加成反應,都可以得到不錯產率及高立體選擇性的加成產物,其鏡像超越值最高可達98% ee。
此合成方法也利用在合成掌性3 - (2 -甲氧基) 苯基吡咯啶 ( α2 -腎上腺素受體拮抗劑) 127和化合物134為HSD-1的抑制劑前驅物。
Chiral α-substituted succimides with various N-protecting groups were
prepared from the asymmetric addition of a range of arylboronic acids to
maleimides in the presence of Rh(I) and chiral diene ligand 77b.
This process offers the chiral α-substituted succimides in good yields
and excellent enantioselectivities (ee values up to 98%) for various
arylboronic acids and maleimides.
This methodology was demonstrated by its utilization in the
enantioselective total synthesis of 3 - (2-methoxyphenyl) pyrrolidine (an
α2-adrenoceptor antagonist) 127 and HSD-1 inhibitor precursor 134.
1.Calne, D. B.; Sandler, M. Nature 1970, 226, 21-24.
2.Seyden-Penne, J. Chiral auxiliaries and ligands in asymmetric synthesis. Wiley New York: 1995.
3.Triem, G. Chem. Ber. 1938, 71, 1522.
4.(a) Betti, M. M., M. Chem. Ber. 1908, 41, 2071; (b) Wheeler, G. P.; Ingersoll, A. W., J. Am. Chem. Soc. 1951, 73, 4604-4606.
5.Kawasaki, T.; Jo, K.; Igarashi, H.; Sato, I.; Nagano, M.; Koshima, H.; Soai, K., Angew. Chem. Int. Ed. 2005, 44, 2774-2777.
6.Blaser, H. U. Chem. Rev. 1992, 92, 935-952.
7.(a) Ojima, I. Catalytic asymmetric synthesis. Wiley: 2010; (b) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive asymmetric catalysis: Supplement. Springer Verlag: 2004; (c) Lin, G. Q.; Li, Y. M.; Chan, A. S. C. Principles and applications of asymmetric synthesis. Wiley Online Library: 2001.
8.Uemura, D. Bioorg. Med. Chem. 2006, 14, 6954-6961 and eited therein
9.Robert, F.; Gao, H Q.; Donia, M.; Merrick, W. C.; Hamann, M. T.; Pettetier, J. RNA 2006, 12, 717-724
10.Malochet-Grivois, C.; Roussakis, C.; Robillard, N.; Biard, J. F.; Riou, D.; Debitus, C.; Verbist, J. F. Anti-Cancer Drug Des. 1992, 7, 493-502
11.Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579-5580.
12.Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
13.Kina, A.; Iwamura, H.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 3904.
14.Chen, F. -X.; Kina, A.; Hayashi, T. Org. Lett. 2006, 8, 341.
15.Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852.
16.Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
17.(a) Brak, K.; Ellman, J. A. J. Org. Chem. 2010, 75, 3147. (b) Pucheault, M.; Darses, S.; Gene ̂ t, J. -P. Eur. J. Org. Chem. 2002, 3552.
18.(a) Pucheault, M.; Darses, S.; Gene ̂ t, J. -P. Tetrahedron Lett. 2002, 43, 6155. (b) Darses, S.; Gene ̂ t, J. -P. Eur. J. Org. Chem. 2003, 4313. (c) Molander, G. A.; Figueroa, R. Aldrichimica Acta 2005, 38, 49.
19.Navarre, L.; Martinez, R.; Gene ̂ t, J. -P.; Darses, S. J. Am. Chem. Soc. 2008, 130, 6159.
20.(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.; Gene ̂ t, J. -P.; Darses, S. Org. Lett. 2009, 11, 3486.
21.(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.
22.(a) Yamamoto, Y.; Takizawa, M.; Yu, X.; Miyaura, N. Angew. Chem., Int. Ed. 2008, 47, 928. (b) Yu, X.; Yamamoto, Y.; Miyaura, N. Synlett .2009, 994.
23.Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2003, 68, 1901.
24.Shintani, R.; Tsutsumi, Y.; Nagaosa, M.; Nishimura, T.; Hayashi, T. J. Am. Chem. Soc. 2009, 131, 13588.
25.Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
26.a) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. (b) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944.
27.Lukin, K.; Zhang, Q. Y.; Leanna, M. R. J. Org. Chem. 2009, 74, 929.
28.Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
29.Yamamoto, Y.; Kurihara, K.; Sugishita, N.; Oshita, K.; Piao, D. G.; Miyaura, N. Chem. Lett. 2005, 34, 1224.
30.Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, H. J. Am. Chem. Soc. 2003, 125, 11508.
31.Shintani, R.; Ueyama, K.; Yamada, I.; Hayashi, T. Org. Lett. 2004, 6, 3425.
32.Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H.,Adv. Synth. Catal. 2001, 343, 264-267.
33.Shintani, R.; Duan, W.-L.; Nagano, T.; Okada, A.; Hayashi, T. Angew. Chem. Int. Ed. 2005, 44, 4611-4614.
34.Duan, L.W.; Lwamura, H.; Shintai, R.;Hayashi, T. J. Am. Chem. Soc. 2007, 129, 2130-2138.
35.Shintani, R.; Duan, L.W.; Hayashi, T. J. Am. Chem. Soc. 2006, 128,5628-5629
36.Luo, Y.; Carnnll, J. A. Angew. Chem. Int. Ed. 2010, 49, 2750-2754.
37.Michelet, V.; Scalone, M.; Millet, A.; d,Herouville, B.L.F. J. Am. Chem. Soc. 2011, 76, 6925-6930.
38.Thaler, T.; Guo, L. N.; Steib, A. K.; Raducan, M.; Karaghiosoff, K.; Mayer, P.; Knochel, P. Org. Lett. 2011, 13, 3182-3185.
39.Vial, R.V.; Ayad, T., Genent, P. J.; Wu, Z.; Berhal, F. J. Org. Chem. 2011, 76, 6320-6326.
40.Defieber, C.; Paquin, J. –F;Serna, S.; Carreira, E. M. Org. Lett. 2004, 6, 3873.
41.Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508.
42.Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584-13585.
43.Leonard, N. J.; Boyer, J. H. J. Org. Chem. 1950, 15, 42-45
44.Lin, G. Q.; Wang, Z. Q.; Feng, C. G.; Xu, M. H. J. Am. Chem. Soc. 2007, 129, 5336.
45.Brown, M. K.; Corey, E. J. Org. Lett. 2010, 12, 172.
46.Allen, M. S.; Darby, N.; Salisbury, P.; Sigurdson, E. R.; Money, T. Can. J. Chem. 1979, 57, 733-741.
47.Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
48.Purves, D.; Augustine, G. J.; Fitzpatrick, D.; Katz, L. C.; Katz, L.; Coquery, J. M.; LaMantia, A. S.; McNamara, J. O.; Williams, M. S. Neurosciences: Avec CD-Rom Sylvius. Le systeme nerveux humain. De Boeck Universite: 2004.
49.M. P. Seiler; J. Nozulak, WO 2001055132.
50.Guzikowski, A. P.; Tamiz, A. P.; Acosta-Burruel, M.; Hong-Bae, S.; Cai, S. X.; Hawkinson, J. E.; Keana, J. F. W.; Kesten, S. R.; Shipp, C. T.; Tran, M.; Whittemore, E. R.; Woodward, R. M.; Wright, J. L.; Zhou, Z.-L. J. Med. Chem. 2000, 43, 984-994.
51.K.Harada; T. Ito, EP 2103603A1.
52.Manteca, L.; Etxarri, B,; Ardeo, A.; Arrasate, S.; Osante, I.; Sotomayor, N.; Lete, E. Tetrahedron. 1998, 54, 12361-12378.
53.Wei, W.-T.; Yeh, J.-Y.; Kuo, T.-S.; Wu, H.-L. Chem. Eur. J. 2011, 17, 11405.
54.Chung, Y.-C.; Janmanchi, D.; Wu, H.-L. Org. Lett. 2012, 14, 2766.
55.Liu, C.-C.; Janmanchi, D.; Chen, C.-C.; Wu, H.-L. Eur. J. Org. Chem. 2012, 2503.