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金鸡纳碱类催化剂在MBH酯的不对称烯丙基烷基化反应中的应用进展

Recent Advance of the Applications of Cinchona Alkaloids Catalysts in Asymmetric Allylic Alkylation of MBH
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摘要 含有手性中心的结构单元被广泛应用于天然产物和药物活性分子(如羟吲哚、苯并呋喃等)中,展现出广泛的生物活性。由于空间位阻等因素的存在,含有立体手性中心(特别是季碳中心)的结构不易合成。MBH酯容易发生烯丙位的取代反应而构建新的碳碳键受到了广泛的关注,烯丙基烷基化反应一般具有条件温和,操作简单,适用性强的特点,金鸡纳碱衍生物是一种在有机化学中广泛应用的手性辅助剂,也是最常用于此类反应的有机催化剂。本论文主要综述了金鸡纳碱类催化剂在MBH酯的不对称烯丙基烷基化反应中的应用。 Abastract: Structural units containing chiral centers were widely applied in a number of pharmaceutically important compounds and natural products(like 2-oxindole,benzofuran) which exhibited broad biological activities. Account for the existence of steric-hindrance,it was difficult for preparing these structures containing chiral frameworks. MBH carbonates were active functional group for allylic alkylation. The cinchona alkaloid derivatives were widely used in such organic reaction as chiral auxiliaries. The asymmetric allylic alkylation of Morita-Baylis-Hillman(MBH) catalyzed by modified cinchona alkaloids were summarized.
出处 《浙江化工》 CAS 2017年第12期23-29,共7页 Zhejiang Chemical Industry
关键词 金鸡纳碱 MBH酯 羟吲哚 烯丙基烷基化 cinchona alkaloid MBH carbonates oxindole allylic alkylation
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  • 1For reviews, see: (a) Das, J. P.; Marek, 1. Chem. Commun. 2011, 47, 4593; (b) Hawner, C.; Alexakis, A. Chem. Commun. 2010, 46, 7295; (c) Bella, M.; Gasperi, T. Synthesis 2009, 1583; (d) Cozzi, E G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969.
  • 2For selected examples of asymmetric construction of spirocyclic 2-oxindoles, see: (a) Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396; (b) Hojo, D.; Noguchi, K.; Hi- rano, M.; Tanaka, K. Angew. Chem. Int. Ed. 2008, 47, 5820; (c) Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819; (d) Bencivenni, G.; Wu, L.-Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M. P.; Bartoli, G.; Melchiorre, P. Angew. Chem. Int. Ed. 2009, 48, 7200; (e) Jiang, K.; Jia, Z.-J.; Chen, S.; Wu, L.; Chert, Y.-C. Chem. Eur. J. 2010, 16, 2852; (f) Jiang, K.; Jia, Z.-J.; Yin, X.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 2766; (g) Antonchick, A. P.; Gerding-Reimers, C.; Ca- tarinella, M.; Schtlrmann, M.; Preut, H.; Ziegler, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2010, 2, 735; (h) Voituriez, A.; Pinto, N.; Neel, M.; Retailleau, P.; Marinetti, A. Chem. Eur J.. 2010, 16, 12541; (i) Jiang, X.; Cao, Y.; Wang, Y.; Liu, L.; Shen, F.; Wang, R. J Am. Chem. Soc. 2010, 132, 15328; (j) Chen, W.-B.; Wu, Z.-J.; Pei, Q.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2010, 12,3132; (k) Zhong, F.; Han, X.; Wang, Y.; Lu, ~. Angew. Chem. lnt. Ed. 2011, 50, 7837.
  • 3For selected examples, see: (a) Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sedeoka, M. J. Am. Chem. Soc. 2005, 127, 10164; (b) Ishimam, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Tom, T.; Shiro, M. Angew. Chem. Ed. Int. 2008, 47, 4157; (c) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Tom, T.; Kane- masa, S. d. Am. Chem. Soc. 2006, 128, 16488; (d) Shaw, S. A.; Ale- man, P.; Christy, J.; Kampf, J. W.; Va, P.; Vedejs, E. J. Am. Chem. Soc. 2006, 128, 925; (e) Ogawa, S.; Shibata, N.; Inagaki, J.; Naka- mura, S.; Tom, T.; Shiro, M. Angew. Chem. Ed. Int. 2007, 46, 8666; (f) Trost, B. M.; Zhang, Y. J.. Am. Chem. Soc. 2007, 129, 14548; (g) Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008, 10, 3583; (h) Jiang, K.; Peng, J.; Cui, H.-L; Chen, Y.-C. Chem. Commun. 2009, 3955; (i) Galzerano, E; Bencivenni, G; Pesciaioli, F.; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem. Eur. J. 2009, 15, 7846; (j) Kato, Y.; Furutachi, M.; Chen, Z.; Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168; (k) Cheng, L.; Liu, L.; Wang, D.; Chen, Y.-J. Org. Left. 2009, 11, 3874; (1) He, R.; Shirakawa, S.; Maruoka, K. d. Am. Chem. Soc. 2009, 131, 16620; (m) Bui, T.; Candeias, N. R.; Barbas, C. F. III. J. Am. Chem. Soc. 2010, 132, 5574.
  • 4, _ w, For selected examples, see: (a) Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sedeoka, M. J. Am. Chem. Soc. 2005, 127, 10164; (b) Ishimam, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Tom, T.; Shiro, M. Angew. Chem. Ed. Int. 2008, 47, 4157; (c) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Tom, T.; Kane- masa, S. d. Am. Chem. Soc. 2006, 128, 16488; (d) Shaw, S. A.; Ale- man, P.; Christy, J.; Kampf, J. W.; Va, P.; Vedejs, E. J. Am. Chem. Soc. 2006, 128, 925; (e) Ogawa, S.; Shibata, N.; Inagaki, J.; Naka- mura, S.; Tom, T.; Shiro, M. Angew. Chem. Ed. Int. 2007, 46, 8666; (f) Trost, B. M.; Zhang, Y. J.. Am. Chem. Soc. 2007, 129, 14548; (g) Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008, 10, 3583; (h) Jiang, K.; Peng, J.; Cui, H.-L; Chen, Y.-C. Chem. Commun. 2009, 3955; (i) Galzerano, E; Bencivenni, G; Pesciaioli, E; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem. Eur. J. 2009, 15, 7846; (j) Kato, Y.; Furutachi, M.; Chert, Z.; Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168; (k) Cheng, L.; Liu, L.; Wang, D.; Chen, Y.-J. Org. Left. 2009, 11, 3874; (1) He, R.; Shirakawa, S.; Maruoka, K. d. Am. Chem. Soc. 2009, 131, 16620; (m) Bui, T.; Candeias, N. R.; Barbas, C. F. III. J. Am. Chem. Soc. 2010. 132. 5574.
  • 5(a) Waldrnann, H.; Khedkar, V.; Dtickert, H.; Schiirmann, M.; Oppel, I. M.; Kumar, K. Angew. Chem. lnt. Ed. 2008, 47, 6869; (b) for a re- view, see: Marcelli, T.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem. lnt. Ed. 2006, 45, 7496.
  • 6For selected examples of organocatalytic asymmetric allylic alkyla- tion of MBH derivatives of aldehydes, see: (a) Cui, H.-L.; Peng, J.;Feng, X.; Du, W.; Jiang, K.; Chen, Y.-C. Chem. Fur. J. 2009, 15, 1574; (b) Cui, H.-L.; Feng, X.; Peng, J.; Lei, J.; Jiang, K.; Chen, Y.-C. Angew. Chem. Int. Ed. 2009, 48, 5737; (c) Huang, J.- R.; Cui, H.-L.; Lei, J.; Sun, X.-H.; Chen, Y.-C. Chem. Commun. 2011, 47, 4784; (d) van Steenis, D. J. V. C.; Marcelli, T.; Lutz, M.; Spek, A. L.; van Maarseveen, A. L. J. H.; Hiemstra, H. Ad~. Synth. Catal. 2007, 349, 281; (e) Jiang, Y.-Q.; Shi, Y.-L.; Shi, M. J. Am. Chem. Soc. 2008, 130, 7202; (f) Ma, Ct-N.; Cao, S.-H.; Shi, M. Tetrahedron: Asymmetry 2009, 20, 1086; (g) Sun, W.; Hong, L.; Liu, C.; Wang, R. Org. Left. 2010, 12, 3914; (h) Yang, W.; Wei, X.; Pan, Y.; Lee, R.; Zhu, B.; Liu, H.; Yan, L; Huang, K.-W.; Jiang, Z.; Tan, C.-H. Chem. Eur. J. 2011, 17, 8066; (i) Lin, A.; Mao, H.; Zhu, X.; Ge, H.; Tan, R.; Zhu, C.; Cheng, Y. Chem. Eur. J. 2011, 17, 13676; (h) For a review, see: Liu, T.-Y.; Xie, M.; Chen, Y.-C. Chem. Soc. Rev. 2012, 41, 4101.
  • 7Xiong, X.-E; Zhang, H.; Peng, J.; Chen, Y.-C. Chem. Eur. J. 2011, 17, 2358.
  • 8CCDC-895875 (41) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cir.
  • 9(a) (~ava, M. P.; Watanabe, Y.; Bessho, K. J. Org. Chem. 1968, 33, 3350; (b) Chen, Z.-C.; Fan, J.-F.; Kende, A. S. J. Org. Chem. 2004, 69, 79.
  • 10(a) Schreiber, S. L. Science 2000, 287, 1964.

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