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2013 , Vol. 33 >Issue 03: 436 - 443

DOI: https://doi.org/10.6023/cjoc201209021

综述与进展

糖基含磷配体在不对称氢化反应中的应用

  • 崔朋雷 ,
  • 刘卉敏 ,
  • 果秀敏 ,
  • 张冬暖 ,
  • 王彦恩 ,
  • 王春
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  • 河北农业大学理学院 保定 071001

收稿日期: 2012-09-14

  修回日期: 2012-11-13

  网络出版日期: 2012-11-20

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Application of Sugar-Based Phosphorus Ligands in Asymmetric Hydrogenation

  • Cui Penglei ,
  • Liu Huimin ,
  • Guo Xiumin ,
  • Zhang Dongnuan ,
  • Wang Yanen ,
  • Wang Chun
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  • College of Science, Agricultural University of Hebei, Baoding 071001

Received date: 2012-09-14

  Revised date: 2012-11-13

  Online published: 2012-11-20

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摘要

不对称氢化反应在实际工业生产中有非常重要的应用. 糖类是广泛存在于自然界的手性天然产物, 手性糖类化合物的合成与应用研究日益受到人们的关注, 以糖类衍生物作为手性配体用于不对称反应已成为有机化学中非常活跃的研究领域. 综述了糖基含磷配体用于不对称氢化反应的最新研究进展.

关键词： 不对称氢化反应; 糖类; 手性配体

本文引用格式

崔朋雷 , 刘卉敏 , 果秀敏 , 张冬暖 , 王彦恩 , 王春 . 糖基含磷配体在不对称氢化反应中的应用[J]. 有机化学, 2013 , 33(03) : 436 -443 . DOI: 10.6023/cjoc201209021

Abstract

There is a very important application for the asymmetric hydrogenation in the actual industrial production. Sugar is chiral natural product which widely exists in the nature. More and more attention was paid to the research of the chiral sugar’s synthesis and application. Sugar derivatives, as chiral ligands, were widely used in asymmetric reactions and the relative research became a very active area in organic chemistry. The recent progress of sugar-based phosphorus-containing ligands that used in asymmetric hydrogenation is reviewed.

Key words： asymmetric hydrogenation; sugar; chiral ligand

参考文献

[1] Hollinsworth, R. I.; Wang, G. Chem. Rev. 2000, 100, 4267.

[2] Boysen, M. M. K. Chem. Eur. J. 2007, 13, 8648.

[3] Zhang, Z.-F.; Xie, F.; Yang, B.; Yu, H.; Zhang, W.-B. Chin. J. Org. Chem. 2011, 31, 429 (in Chinese).
(张振锋, 谢芳, 杨波, 余焓, 张万斌, 有机化学, 2011, 31, 429.)

[4] Wang, Y.-D.; Wang, F.; Miao, Z.-W.; Chen, R.-Y. Prog. Chem. 2008, 20, 1923 (in Chinese).
(王亚丹, 王飞, 苗志伟, 陈茹玉, 化学进展, 2008, 20, 1923.)

[5] Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Chem. Ber. 1986, 119, 3326.

[6] Nagel, U.; Rieger, B. Organometallics 1989, 8, 1534.

[7] Lafont, D.; Sinou, D.; Descotes, G. J. Organomet. Chem. 1979, 169, 87.

[8] Bakos, J.; Heil, B.; Markó, L. J. Organomet. Chem. 1983, 253, 249.

[9] Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62.

[10] Li, C.; Bernet, B. B.; Vasella, A.; Broger, E. A.; Meili, A. Carbohydr. Res. 1991, 149.

[11] Choudary, B. M.; Sarma, M. R.; Prasad, A. D.; Narender, N. Indian J. Chem. B 1994, 33, 152.

[12] Gilbertson, S. R.; Chang, C. W. T. J. Org. Chem. 1995, 60,6226.

[13] Brunner, H.; Sievi, R. J. Organomet. Chem. 1987, 328, 71.

[14] Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76.

[15] Yamashita, M.; Hiramatsu, K.; Yamada, M.; Suzuki, N.; Inokawa, S. Bull. Chem. Soc. Jpn. 1982, 55, 2917.

[16] Saito, S.; Nakamura, Y.; Morita, Y. Chem. Pharm. Bull. 1985, 33, 5284.

[17] Iida, A.; Yamashita, M. Bull. Chem. Soc. Jpn. 1988, 61, 2356.

[18] Lemaux, P.; Massonneau, V.; Simonneaux, G. J. Organomet. Chem. 1985, 284, 101.

[19] Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Eur. J. Inorg. Chem. 2000, 2011.

[20] Diéguez, M.; Pamies, O.; Ruiz, A.; Castillon, S.; Claver, C. Tetrahedron: Asymmetry 2000, 11, 4701.

[21] Gridenev, I. D.; Higashi, N.; Asakura, K.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 7183.

[22] Wong, Y. T.; Yang, C.; Ying, K. C.; Jia, G. Organometallics 2002, 21, 1782.

[23] Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 19, 1635.

[24] Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29.

[25] Selke, R. React. Kinet. Catal. Lett. 1979, 10, 135.

[26] Sinou, D.; Descotes, G. React. Kinet. Catal. Lett. 1980, 14, 463.

[27] Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213.

[28] Selke, R. J. Prakt. Chem. 1987, 4, 717.

[29] Selke, R. J. Organomet. Chem. 1989, 370, 249.

[30] Selke, R.; Scwarze, M.; Baudishi, H.; Grassert, I.; Michalik, M.; Oehme, G.; Costisella, B. J. Mol. Catal. 1993, 84, 223.

[31] Selke, R.; Ohff, M.; Riepe, A. Tetrahedron 1996, 52, 15079.

[32] RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.

[33] RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1992, 62, 6012.

[34] Ayers, T. A.; RajanBabu, T. V. US 5510507, 1996 [Chem. Abstr. 1995, 124, 9449].

[35] Yan, Y. Y.; RajaBabu, T. V. J. Org. Chem. 2001, 66, 3277.

[36] Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967.

[37] Yonehara, K.; Ohe, K.; Uemura. S. J. Org. Chem. 1999, 64, 9381.

[38] Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593.

[39] Chen, Y.; Li, X.; Tong, S.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957.

[40] Naili, S.; Suisse, I.; Mortreux, A.; Agbossou, F.; Ali, M. A.; Karim, A. Tetrahedron Lett. 2000, 41, 2867.

[41] Guimet, E.; Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2004, 15, 2247.

[42] Aghmiz, M.; Aghmiz, A.; Diaz, Y.; Masdeu-Bulto, A. M.; Claver, C.; Castillon, S. J. Org. Chem. 2004, 69, 7502.

[43] Guiu, E.; Munoz, B.; Castillon, S.; Claver, C. Adv. Synth. Catal. 2003, 345, 169.

[44] Kadyrov, R.; Heller, D.; Selke, R. Tetrahedron: Asymmetry 1999, 9, 329.

[45] Reetz, M. T.; Neugebauer, T. Angew. Chem. Int. Ed. 1999, 38, 179.

[46] Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Eur. J. Inorg. Chem. 2000, 1287.

[47] Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2000, 11, 1097.

[48] Diéguez, M.; Ruiz, A.; Claver, C. J. Org. Chem. 2002, 67, 3796.

[49] Axet, M. R.; Benet-Buchholz, J.; Claver, C.; Castillon, S. Adv. Synth. Catal. 2007, 349, 1983.

[50] Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889.

[51] Reetz, M. T.; Goosen, L. J.; Meiswinkel, A.; Paetzol, J.; Jensen, J. F. Org. Lett. 2003, 5, 3099.

[52] Huang, H.; Zheng, Z.; Luo, H.; Bai, C.; Hu, X.; Chen, H. Org. Lett. 2003, 5, 4137.

[53] Huang, H.; Liu, X.; Chen, S.; Chen, H.; Zheng, Z. Tetrahedron: Asymmetry 2004, 15, 2011.

[54] Huang, H.; Zheng, Z.; Luo, H.; Bai, C.; Hu, X.; Chen, H. J. Org. Chem. 2004, 69, 2335.

[55] Huang, H.; Liu, X.; Chen, H.; Zheng, Z. Tetrahedron: Asymmetry 2005, 16, 693.

[56] Zhao, Y.; Huang, H.; Shao, J.; Xia, C. Tetrahedron: Asymmetry 2011, 22, 769.

[57] Reetz, M. T.; Gosberg, A. Tetrahedron: Asymmetry 1999, 10, 2129.

[58] Ohe, K.; Morioka, K.; Yonehara, K.; Uemura, S. Tetrahedron: Asymmetry 2002, 13, 2155.

[59] Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. Chem. Commun. 2000, 2383.

[60] Pàmies, O.; Dieguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364.

[61] Diéguez, M.; Ruiz, A.; Claver, C. Chem. Commun. 2001, 2072.

[62] Guiu, E.; Aghmiz, M.; Diaz, Y.; Claver, C. Meseguer, B.; Militzer, C.; Castillon, S. Eur. J. Org. Chem. 2006, 627.

[63] Diéguez, M.; Mazuela, J.; Pàmies, O.; Verendel, J. J.; Andersson, P. G. J. Am. Chem. Soc. 2008, 130, 7208.

[64] Mazuela, J.; Norrby, P. O.; Andersson, P. G.; Pàmies, O.; Diéguez, M. J. Am. Chem. Soc. 2011, 133, 13634.

[65] Margalef, J.; Lega, M.; Ruffo, F.; Pàmies, O.; Diéguez, M. Tetrahedron: Asymmetry 2012, 23, 945.

[66] Khiar, N.; Suarez, B.; Stiller, M.; Valdivia, V.; Fernandez, I. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 1253.

[67] Khiar, N.; Navas, R.; Suarez, B.; Alvarez, E.; Fernandez, I. Org. Lett. 2008, 10, 3697.

[68] Guimet, E.; Dieguez, M.; Ruiz, A.; Claver, C. Dalton Trans. 2005, 2557.
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