SIOC English
化学学报
高级检索

化学学报 >

2013 , Vol. 71 >Issue 01: 40 - 43

DOI: https://doi.org/10.6023/A12110850

研究通讯

聚乙二醇负载的二茂铁噁唑啉配体的合成及其应用

  • 刘洪强 ,
  • 时磊 ,
  • 陈庆安 ,
  • 王磊 ,
  • 周永贵
展开
  • a 中国科学院大连化学物理研究所 大连 116023;
    b 淮北师范大学 淮北市 235000

收稿日期: 2012-11-01

  网络出版日期: 2012-12-10

基金资助

项目受国家自然科学基金(Nos. 21202162 and 21125208)和国家重大基础研究项目(No. 2010CB833300)资助.

收起

Synthesis of MeO-PEG-Supported Ferrocenyloxazoline Ligands and Their Application in Asymmetric Catalysis

  • Liu Hongqiang ,
  • Shi Lei ,
  • Chen Qingan ,
  • Wang Lei ,
  • Zhou Yonggui
Expand
  • a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China;
    b Huaibei Normal University, Huaibei 235000, China

Received date: 2012-11-01

  Online published: 2012-12-10

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21202162 & 21125208) and the National Basic Research Program of China (No. 2010CB833300).

Fold

摘要

报道了聚乙二醇(MeO-PEG)负载的二茂铁噁唑啉衍生的手性N,P和N,S配体的合成. 所得负载N,P配体可以成功应用于银催化的[3+2]环加成反应, 最高取得了97%的对映选择性. 另外聚乙二醇负载二茂铁N,S配体可以成功应用于钯催化的烯丙基取代反应, 取得了90%的ee值. 值得注意是, 聚乙二醇负载形成的催化剂循环使用4次后其催化活性和选择性仍可基本保持.

关键词： 聚乙二醇; 二茂铁噁唑啉; 不对称催化

本文引用格式

刘洪强 , 时磊 , 陈庆安 , 王磊 , 周永贵 . 聚乙二醇负载的二茂铁噁唑啉配体的合成及其应用[J]. 化学学报, 2013 , 71(01) : 40 -43 . DOI: 10.6023/A12110850

Abstract

A simple synthesis of ferrocenyloxazoline derived chiral N,P ligands and N,S ligands immobilized on a MeO- PEG-support is described. The metal complexes of chiral ligands have been successfully applied to 1,3-dipolar cycloaddition reaction of azomethine ylides and asymmetric allylic substitution reaction, providing the products with up to 97% ee and 90% ee, respectively. The MeO-PEG-supported metal complex catalysts can be recycled easily and reused.

Key words： PEG; ferrocenyloxazoline ligands; asymmetric catalysis

参考文献

[1] Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.

[2] Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325.

[3] Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.

[4] Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.

[5] Han, H. S.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632.

[6] Reger, T. S.; Janda, K. D. J. Am. Chem. Soc. 2000, 122, 6929.

[7] Fan, Q. H.; Deng, G. J.; Lin, C. C.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1241.

[8] Li, X. G.; Chen, W. P.; Hems, W.; King, F.; Xiao, J. L. Org. Lett. 2003, 5, 4559.

[9] Gissibl, A.; Finn, M. G.; Reiser, O. Org. Lett. 2005, 7, 2325.

[10] Xu, L.; Lam, K. H.; Ji, J.; Wu, J.; Fan, Q.-H.; Lo, W.-H.; Chan, A. S. C. Chem. Commun. 2005, 1390.

[11] Yang, X. W.; Liu, H. Q.; Xu, M. H.; Lin, G. Q. Chin. J. Chem. 2005, 23, 68.

[12] Hu, X. P.; Huang, J. D.; Zeng, Q. H.; Zheng, Z. Chem. Commun. 2006, 293.

[13] Bandini, M.; Benaglia, M.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. Org. Lett. 2007, 9, 2151.

[14] Wang, X. B.; Zhou, Y. G. J. Org. Chem. 2008, 73, 5640.

[15] Dai, L. X.; Tu, T.; You, S. L.; Deng, W. P.; Hou, X. L. Acc. Chem. Res. 2003, 36, 659.

[16] Arrayas, R. G.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 7674.

[17] Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505.

[18] Naodovic, M.; Yamamoto, H. Chem. Rev. 2008, 108, 3132.

[19] Yanagisawa, A.; Arai, T. Chem. Commun. 2008, 1165.

[20] Chen, Q. A.; Wang, D. S.; Zhou, Y. G. Chem. Commun. 2010, 46, 4043.

[21] Zeng, W.; Zhou, Y. G. Org. Lett. 2005, 7, 5055.

[22] Zeng, W.; Chen, G. Y.; Zhou, Y. G.; Li, Y. X. J. Am. Chem. Soc. 2007, 129, 750.

[23] Zeng, W.; Zhou, Y. G. Tetrahedron Lett. 2007, 48, 4619.

[24] Chen, Q. A.; Zeng, W.; Wang, D. W.; Zhou, Y. G. Synlett 2009, 2236.

[25] Chen, Q. A.; Zeng, W.; Zhou, Y. G. Tetrahedron Lett. 2009, 50, 6866.

[26] Bolm, C.; Hermanns, N.; Classen, A.; Muniz, K. Bioorg. Med. Chem. Lett. 2002, 12, 1795.

[27] Martin-Matute, B.; Isabel Pereira, S.; Pena-Cabrera, E.; Adrio, J.; Silva, A. M. S.; Carretero, J. C. Adv. Synth. Catal. 2007, 349, 1714.

[28] Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1.

[29] Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.

[30] Deng, H. B.; Jung, J. K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 9032.

[31] Liao, L. A.; Zhang, F.; Dmitrenko, O.; Bach, R. D.; Fox, J. M. J. Am. Chem. Soc. 2004, 126, 4490.

[32] Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419.

[33] You, S. L.; Zhou, Y. G.; Hou, X. L.; Dai, L. X. Chem. Commun. 1998, 2765.

[34] Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.

[35] Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484.

[36] Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887.

[37] Gothelf, A. S.; Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 4236.

[38] Longmire, J. M.; Wang, B.; Zhang, X. M. J. Am. Chem. Soc. 2002, 124, 13400.

[39] Chen, C.; Li, X. D.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174.

[40] Cabrera, S.; Arrayas, R. G.; Carretero, J. C. J. Am. Chem. Soc. 2005, 127, 16394.

[41] Saito, S.; Tsubogo, T.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 5364.

[42] Chen, X. H.; Zhang, W. Q.; Gong, L. Z. J. Am. Chem. Soc. 2008, 130, 5652.

[43] Shi, J. W.; Zhao, M. X.; Lei, Z. Y.; Shi, M. J. Org. Chem. 2008, 73, 305.

[44] Najera, C.; Retamosa, M. D.; Sansano, J. M. Angew. Chem., Int. Ed. 2008, 47, 6055.

[45] Wang, C. J.; Liang, G.; Xue, Z. Y.; Gao, F. J. Am. Chem. Soc. 2008, 130, 17250.

[46] Wang, C. J.; Xue, Z. Y.; Liang, G.; Lu, Z. Chem. Commun. 2009, 2905.

[47] Xue, Z. Y.; Liu, T. L.; Lu, Z; Huang, H.; Tao, H. Y.; Wang, C. J. Chem. Commun. 2010, 1727.

[48] Kim, H. Y.; Shih, H. J.; Knabe, W. E.; Oh, K. Angew. Chem., Int. Ed. 2009, 48, 7420.

[49] Arai, T.; Mishiro, A.; Yokoyama, N.; Suzuki, K.; Sato, H. J. Am. Chem. Soc. 2010, 132, 5338.

[50] Yamashita, Y.; Imaizumi, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2011, 50, 4893.

[51] You, S. L.; Hou, X. L.; Dai, L. X.; Yu, Y. H.; Xia, W. J. Org. Chem. 2002, 67, 4684.

Options
文章导航

/

〈 〉