簡易檢索 / 詳目顯示

回結果列表
研究生： 辜卡力
論文名稱： 酮醯胺衍生物進行不對稱還原反應
diasetereoselective allylation of chiral glyoxylic oxime ethers and reduction of N-phenyl camphorpyrazolidinone derived a-keto amides
指導教授： 陳焜銘
學位類別： 博士
Doctor
系所名稱： 化學系
Department of Chemistry
論文出版年： 2006
畢業學年度： 94
語文別： 中文
中文關鍵詞： 烯丙胺 、樟腦衍生物 、還原反應
論文種類： 學術論文
相關次數： 點閱：165  下載：0 
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

    • 外籍學生無中文摘要

    In the first part of this monograph, various chiral glyoxylic oximes were prepared to develop a new route to synthesize chiral α-amino amides, which are synthetic intermidiates of α-amino acids. The allylation of camphor sultam derived glyoxylic oxime ether by allyltributyltin in the presence of Lewis acids Zn(OTf)2, AgOTf, Sn(OTf)2 provided homoallylic α-amino amides, and Sn(OTf)2 emerged as the best Lewis acid when tested in allylation of various chiral glyoxylic oxime ethers. To continue the research in allylation of glyoxylic oxime ether, we studied allylation by using triallylaluminium. The reaction of triallylaluminium with chiral glyoxylic oxime ethers provided homoallylic amine products up to > 99% diastereoselectivity.
    In the following parts, we have investigated the scope of N-phenyl camphorpyrazolidinone in synthetic organic chemistry. When N-phenyl camphorpyrazolidinone derived α-keto amides employed in hydride reduction, the hydride reduction of aliphatic and aromatic α-keto amides provided corresponding α-hydroxy amides in excellent yields and very high level of diastereoselectivities.

    1 Diastereoselective allylation of chiral glyoxylic oxime ether 1 1.1. Asymmetric allylation in the presence of Lewis acid 13 1.1.1 Asymmetric allylation to C=N 24 1.1.2 Diastereoselective allylation of camphor sulam derived glyoxylic oxime ethers 25 1.1.3 Diastereoselective allylation of chiral glyoxylic oxime ethers in the presence of Lewis acid 27 1.2 Diastereoselective allylation of chiral glyoxylic oxime ethers by triallylaluminium 37 1.2.1 Allylation by using allylaluminium reagent 38 1.2.2 Diastereoselective allylation by using triallylaluminium 40 1.3 Conclusion 45 2 Reduction of N-phenyl Camphorpyrazolidinone derived α-ketoamide 47 2.1 Asymmetric reduction ketones 47 2.2 Diastereoselective reduction of N-phenyl Camphorpyrazolidinone derived α-ketoamide 49 2.3 Conclusion 52 3 Alkyl radical reaction of N-phenyl Camphorpyrazolidinone 53 derived glyoxylic oxime ether 3.1 Radical reaction 53 3.2 Acyclic asymmetric radical reaction 54 3.2.1 Chiral Lewis acid controlled stereoselective radical reaction 54 3.2.1 Chiral substrate controlled stereoselective radical reaction 56 3.3 Diasteoselective alkyl radical reaction of camphorsultam derived glyoxylic oxime ether 57 3.4 Diasteoselective alkyl radical reaction of N-phenyl Camphor- pyrazolidinone derived glyoxylic oxime ether 59 3.5 Conclusion 61 4. Reactions of N-phenyl camphorpyrazolidinone derived sulfonium salt 62

    1 (a) Brenna, E.; Fuganti, C.; Serra, S. Tetrahedron Asymm. 2003, 14, 1. (b) Brown, H. C.; Ramchandran, P. V. J. Orgamet. Chem., 1995, 500, 1
    2 Xu, P.-F.; Chen, Y.-S.; Lin, S.-I.; Lu, T.-J. J. Org. Chem., 2002, 67, 2309.
    3 Workman, J. A.; Garrido, N. P.; Sancon, J.; Roberts, E.; Wessel, H. P.; Sweeney, J. B. J. Am. Chem. Soc. 2005, 127, 1066.
    4 Rajaram, S.; Sigman, M. S. Org. Lett., 2005, 7, 5473.
    5 Lee, J.; Lee, Y.-I.; Kang, M. J.; Lee, Y.-J.; Jeong, B.-S.; Lee, J.-H.; Kim, M.-J.; Choi, J.-y.; Ku, J.-M.; Park, H.-g.; Jew, S.-S. J. Org. Chem. 2005; 70, 4158.
    6 Aggarwal, V. K.; Charmant, J. P. H.; Fuentes, D.; Harvey, J. N.; Hynd, G.; Ohara, D.; Picoul, W.; Robiette, R.; Smith, C.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2006, 128, 2105.
    7 Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lain, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993.
    8 Yang, K.-S.;. Chen, K. Org. Lett. 2000, 2, 729.
    9 Yang, K.-S.; Lain, J.-C.; Lin, C.-H.; Chen, K. Tetrahydron. Lett. 2000, 41, 1453.
    10 Lin, C.-H.; Yang, K.-S.; Pan, J.-F. Chen, K. Tetrahydron. Lett. 2000, 41, 6815.
    11 Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676.
    12 Fan, C. L.; Lee, W.-D.; Teng, N.-W.; Sun, Y.-C.; Chen, K. J. Org. Chem. 2003, 66, 9816.
    13 Pan, J.-F.; Chen, K. Tetrahydron. Lett. 2004, 45, 2541.
    14 Wang, S.-G.; Tsai, H. R.; Chen, K. Tetrahydron. Lett. 2004, 45, 6185.
    15 Pan, J.-F.; Venkatesham, U; Chen, K. Tetrahydron. Lett. 2004, 45, 9345.
    16 Chen, J.-H.; Venkatesham, U; Chen, K. Tetrahydron. 2006, 62, 887.
    17 Denmark, S. E.; Fu, J. Chem. Rev. 2003.
    18 Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem., 2002, 39, 595.
    19 Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry: Otera, J.; Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10 and references therein.
    20 Shimizu, M.; Kimura, M.; Watanabe, T.; Tamaru, Y. Org. Lett., 2005, 7, 637.
    21 Solin, N.; Wallner, O. A.; Szabo, K. J. Org. Lett., 2005, 7, 689.
    22 Fernandes, R. A.; Yamamoto, Y. J. Org. Chem., 2004, 69, 735.
    23 Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev., 2003, 103, 3155.
    24 Berger, R.; Rabbat, P. M.; Leighton, J. L. J. Am. Chem. Soc., 2003, 125, 9596.
    25 Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc., 2003, 125, 6610.
    26 Hamada, T.; Manabe, K.; Kobayashi, S. Angew. Chem. Int. Ed. 2003, 42, 3927.
    27 Bates, R. B.; Beavers, W. A.; Gordon, B., III; Mills, M. S. J. Org. Chem., 1979, 44, 3800.
    28 Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Itoh, W. J. Am. Chem. Soc., 1986, 108, 7778.
    29 Schuetz R. D; Houff W. H. J. Am. Chem. Soc.1955, 77, 1839.
    30 Walmann,H. Synlett., 1990, 627.
    31 Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586.
    32 Denmark, S. E.; Fu, J. Chem. Rev., 2003, 103, 2763.
    33 Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
    34 Hamasaki, R; Chounan, Y.; Horino, H.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 9883.
    35 Sibi, M. P.; Rheault, T. R. J. Am. Chem. Soc. 2002, 122, 8873.
    36 Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
    37 Kim, J. G.; Waltz, K. M.; Garcia, I. F.; Kwiatkowski, D.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 12580.
    38 Denmark, S. E.; Coe, D. M; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161.
    39 Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. J. Am. Chem. Soc. 1998, 120, 6419.
    40 Wu, T. R.; Shen, L.; Chong, M. Org. Lett., 2004, 6, 2702.
    41 Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920.
    42 Kulesza, A.; Mieczkowski, A.; Jurczak, J. Tetrahedron Asymm. 2002, 13, 2061.
    43 Kiegiel, K.; Balakier, T.; Kwiatkowski, P.; Jurczak, J. Tetrahedron Asymm. 2004, 15, 3869.
    44 Fernandes, R. A.; Stimac, A.; Yamamoto, Y. J. Am. Chem. Soc., 2003, 125, 14133; Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
    45 Cook, G. R.; Maity, B. C.; Kargbo, R. Taylor, R. E.; Jin, M. Org. Lett. 2004, 6, 1741.
    46 Hanessian, S.; Yang, R.- Y. Tetrahedron Lett. 1996, 37, 5273.
    47 Miyabe, H.; Nishimura, A.; Ueda, M.; Naito, T. Chem. Commun., 2002, 14, 1454.
    48 Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem., 2003, 68, 6745.
    49 Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem., 2004, 69, 1415.
    50 Ashby, E. C.; Noding, S. A. J. Org. Chem. 1979, 44, 4792.
    51 Ruano, J. L. G.; Tito, A.; Culebras, R. Tetrahedron 1996, 52, 2177.
    52 Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4573.
    53 Yamamoto, Y.; Komatsu, T., Maruyama, K. Chem. Commun. 1985, 11, 814.
    54 Minowa, N.; Mukaiyama, T. Bull. Chem. Soc. Jpn., 1987, 60, 3697.
    55 You, J.-S.; Hsieh, S.-H.; Gau, H.-M. Chem. Commun. 2001, 11, 1546.
    56 Rainier, J. D.; Cox, J. M. Org. Lett. 2000, 2, 2707.
    57 Wagner, C. E.; Kim, J.-S.; Shea, K. J. J. Am. Chem. Soc. 2003, 125, 12179.
    58 Garcia Ruano, J. L.; Fernandez-Ibanez, M. A.; Maestro, M. C.; Rodriguez-Fernandez, M. M. J. Org. Chem. 2005, 70, 1796.
    59 Ramachandran, P. V.; Brown, H. C.; Pitre, S. Org. Lett. 2001, 3, 17.
    60 Hom, R. K.; Fang, L. Y.; Mamo, S.; Tung, J. S.; Guinn, A. C.; Walker, D. E.; Davis, D. L.; Gailunas, A. F.; Thorsett, E. D.; Sinha, S.; Knops, J. E.; Jewett, N. E.; Anderson, J. P.; John, V. J. Med. Chem. 2003, 46, 1799.
    61 Nizi, E.; Koch, U.; Ponzi, S.; Matassa, V. G.; Gardelli, C. Bioorg. Med. Chem. Lett. 2002, 12, 3325.
    62 Deechongkit, S.; You, S.-L.; Kelly, J. W. Org. Lett. 2004, 6, 497.
    63 Fukuzawa, S.-i.; Miura, M.; Matsuzawa, H. Tetrahedron Lett. 2001, 42, 4167.
    64 Scafato, P.; Leo, L.; Superchi, S.; Rosini, C. Tetrahedron 2002, 58, 153.
    65 N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 297.
    66 Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem.Soc. 1995, 117, 11029.
    67 Sibi, M. P.; Sausker, J. B. J. Am. Chem.Soc. 2002, 124, 984.
    68 Sibi, M. P.; Ji, J. J. Org. Chem., 1996, 61, 6090.
    69 Fernandez, M.; Alonso, R. Org. Lett. 2003, 5, 2461.
    70 Hart, D. J.; Seely F. L. J. Am. Chem. Soc. 1988, 110, 1631.
    71 Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun., 1997, 1789
    72 Miyabe, H.; Fujii, K.; Naito, T. Org. Lett. 1999, 1, 569.
    73 Miyabe, H.; Ushiro, C.; Ueda, M.; Yamakawa, K.; Naito, T. J. Org. Chem., 2000, 65, 176.
    74 Furukawa, N.; Sugihara, Y.; Fujihara, H. J. Org. Chem. 1989, 54, 4222.
    75 Aggarwal, V. K.; Abdel-Rahman, H.; Jones, R. V. H.; Lee, H. Y.; Reid, B. D. J.Am. Chem. Soc. 1994, 116, 5973.
    76 Aggarwal, V. K.;Thompson, A.; Jones, R. V. H.; Standen, M. Tetrahedron: Asymmetry. 1995, 6, 2557.
    77 Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J.Am. Chem. Soc. 1996, 118, 7004.
    78 Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489.

    無法下載圖示
    QR CODE