综述与进展

非对称杂化的手性膦-亚磷酰胺酯配体在不对称催化反应中的应用进展

  • 侯传金 ,
  • 刘小宁 ,
  • 夏英 ,
  • 胡向平
展开
  • a 大连工业大学轻工与化学工程学院 大连 116034;
    b 中国科学院大连化学物理研究所 大连 116023

收稿日期: 2012-05-30

  修回日期: 2012-07-17

  网络出版日期: 2012-07-18

基金资助

大连市科技局科技计划项目(No. 2011J21DW010)和辽宁省教育厅科学技术研究(No. L2010048)资助项目.

Progress on Unsymmetrical Hybrid Chiral Phosphine-phosphoramidite Ligands and Their Application in Asymmetric Catalytic Reactions

  • Hou Chuanjin ,
  • Liu Xiaoning ,
  • Xia Ying ,
  • Hu Xiangping
Expand
  • a School of Light Industry and Chemical Engineering, Dalian Polytechnic University, Dalian 116034;
    b Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023

Received date: 2012-05-30

  Revised date: 2012-07-17

  Online published: 2012-07-18

Supported by

Project supported by the Planned Science and Technology Project of Dalian City (No. 2011J21DW010), and the Scientific Research Project of Department of Education of Liaoning Province (No. L2010048).

摘要

非对称杂化的手性膦-亚磷酰胺酯配体因其合成简便、易于调控、结构稳定等优点, 被广泛应用于不对称催化反应中, 如: 不对称氢化、不对称氢甲酰化、不对称烯丙基烷基化、不对称氢膦酰化、不对称[3+2]-环加成、不对称1,4-加成和1,4-还原反应等. 综述了手性膦-亚磷酰胺酯配体的种类、合成及其在不对称催化反应中的应用.

本文引用格式

侯传金 , 刘小宁 , 夏英 , 胡向平 . 非对称杂化的手性膦-亚磷酰胺酯配体在不对称催化反应中的应用进展[J]. 有机化学, 2012 , 32(12) : 2239 -2247 . DOI: 10.6023/cjoc201205035

Abstract

Unsymmetrical hybrid chiral phosphine-phosphoramidite ligands have the advantages of easy accessibility, modularity and stability toward air and moisture, which make them highly appealing for asymmetric catalysis. These ligands have been found widespread utility in asymmetric catalysis, such as hydrogenation, hydroformylation, allylic alkylation, hydrophosphorylation, [3+2] cycloaddition, 1,4-addition and 1,4-reduction. The types, synthesis and applications of chiral phosphine-phosphoramidite ligands are reviewed.

参考文献

[1] Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999.

[2] Ojima, I. Catalytic Asymmetric Synthesis, Wiley-VCH, Weinheim, 2000.

[3] Thommen, M.; Hlaser, H.-U. In Phosphorus Ligands in Asymmetric Catalysis, Ed.: Brner A., Wiley-VCH, Weinheim, 2008.

[4] Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.

[5] Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.

[6] Zhang, W.; Chi, Y.; Zhang, X. Acc. Chem. Res. 2007, 40, 1278.

[7] Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481.

[8] Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.

[9] Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.

[10] Berthod, M.; Migani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801.

[11] Ding, K.; Guo, H.; Li, X.; Yuan, Y.; Wang, Y. Top. Catal. 2005, 35, 105.

[12] Ding, K.; Li, X.; Ji, B.; Guo, H.; Kitamura, M. Curr. Org. Synth. 2005, 2, 499.

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

[14] Tang, W.; Xu, L.; Fan, Q.-H.; Wang, J.; Fan, B.; Zhou, Z.; Lam, K.-H.; Chan, A. S. C. Angew. Chem., Int. Ed. 2009, 48, 9135.

[15] Arshad, N.; Kappe, C. O. Adv. Heterocycl. Chem. 2010, 99, 33.

[16] Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.

[17] Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Hariow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.

[18] Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. 1998, 37, 1931.

[19] Tang, W.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 612.

[20] Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 646.

[21] Shang, G.; Yang, Q.; Zhang, X. Angew. Chem., Int. Ed. 2006, 45, 6360.

[22] Gridnev, I. D.; Imamoto, T.; Hoge, G.; Kouchi, M.; Takahashi, H. J. Am. Chem. Soc. 2008, 130, 2560.

[23] Zhang, X.; Huang, K.; Hou, G.; Cao, B.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 6421.

[24] Boeda, T.; Beneyton, T.; Crévisy, C. Mini-Rev. Org. Chem. 2008, 5, 96.

[25] Eberhardt, L.; Armspach, D.; Harrowfield, J.; Matt, D. Chem. Soc. Rev. 2008, 839.

[26] Hu, X.-P.; Wang, D.-S.; Yu, C.-B.; Zhou, Y.-G.; Zheng, Z. Top. Organomet. Chem. 2011, 36, 343.

[27] Wassenaar, J.; Reek, J. N. H. Org. Biomol. Chem. 2011, 9, 1704.

[28] Franciò, C.; Faraone, F.; Leitner, W. Angew. Chem., Int. Ed. 2000, 39, 1428.

[29] Wassenaar, J.; van Zutphen, S.; Mora, G.; Floch, P. L.; Siegler, M. A.; Spek, A. L.; Reek, J. N. H. Organometallics 2009, 28, 2724.

[30] Hu, X.-P.; Zheng, Z. Org. Lett. 2004, 6, 3585.

[31] Jia, X.; Li, X.; Lam, W. S.; Kok, S. H. L.; Xu, L.; Lu, G.; Yeung, C.-H.; Chan, A. S. C. Tetrahedron: Asymmetry 2004, 15, 2273.

[32] Huang, J.-D.; Hu, X.-P.; Duan, Z.-C.; Zeng, Q.-H.; Yu, S.-B.; Deng, J.; Wang, D.-Y.; Zheng, Z. Org. Lett. 2006, 8, 4367.

[33] Zhang, W.; Zhang, X. Angew. Chem., Int. Ed. 2006, 45, 5515.

[34] Balogh, S.; Farkas, G.; Madarász, J.; Szöll?sy, Á.; Kovács, J.; Darvas, F.; Ürge, L.; Bakos, J. Green. Chem. 2012, 14, 1146.

[35] 35 Qiu, M.; Wang, D.-Y.; Hu, X.-P.; Huang, J.-D.; Yu, S.-B.; Deng, J.; Duan, Z.-C.; Zheng, Z. Tetrahedron: Asymmetry 2009, 20, 210.

[36] Pullmann, T.; Engendahl, B.; Zhang, Z.; Hoelscher, M.; Zanotti- Gerosa, A.; Dyke, A.; Francio, G.; Leitner, W. Chem. Eur. J. 2010, 16, 7517.

[37] Hu, X.-P.; Zheng, Z. Org. Lett. 2005, 7, 419.

[38] Zhou, X.-M.; Huang, J.-D.; Luo, L.-B.; Zhang, C.-L.; Hu, X.-P.; Zheng, Z. Org. Biomol. Chem. 2010, 8, 2320.

[39] Vallianatou, K. A.; Kostas, I. D.; Holz, J.; Börner, A. Tetrahedron Lett. 2006, 47, 7947.

[40] Eggenstein, M.; Thomas, A.; Theuerkauf, J.; Francio, G.; Leitner, W. Adv. Synth. Catal. 2009, 351, 725.

[41] Schäffner, B.; Schäffner, F.; Verevkin, S. P.; Börner, A. Chem. Rev. 2010, 110, 4554.

[42] Zhang, W.; Zhang, X. J. Org. Chem. 2007, 72, 1020.

[43] Wassenaar, J.; Reek, J. N. H. J. Org. Chem. 2009, 74, 8403.

[44] Wassenaar, J.; Kuil, M.; Lutz, M.; Spek, A. L.; Reek, J. N. H. Chem. Eur. J. 2010, 16, 6509.

[45] Wang, D.-Y.; Hu, X.-P.; Huang, J.-D.; Deng, J.; Yu, S.-B.; Duan, Z.-C.; Xu, X.-F.; Zheng, Z. Angew. Chem., Int. Ed. 2007, 46, 7810.

[46] Qiu, M.; Hu, X.-P.; Wang, D.-Y.; Deng, J.; Huang, J.-D.; Yu, S.-B.; Duan, Z.-C.; Zheng, Z. Adv. Synth. Catal. 2008, 350, 1413.

[47] Yu, S.-B.; Huang, J.-D.; Wang, D.-Y.; Hu, X.-P.; Deng, J.; Duan, Z.-C.; Zheng, Z. Tetrahedron: Asymmetry 2008, 19, 1862.

[48] Burk, S.; Franciò, G.; Leitner, W. Chem. Commun. 2005, 3460.

[49] Wassenaar, J.; Reek, J. N. H. Dalton Trans. 2007, 3750.

[50] Wassenaar, J.; de Bruin, B.; Reek, J. N. H. Organometallics 2010, 29, 2767.

[51] Chikkali, S. H.; Bellini, R.; de Bruin, B.; van der Vlugt, J. I.; Reek, J. N. H. J. Am. Chem. Soc. 2012, 134, 6607.

[52] Yan, Y.; Zhang, X. J. Am. Chem. Soc. 2006, 128, 7198.

[53] Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413.

[54] Zhang, X.; Cao, B.; Yan, Y.; Yu, S.; Ji, B.; Zhang, X. Chem Eur. J. 2010, 16, 871.

[55] Zhang, X.; Cao, B.; Yu, S.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 4047.

[56] Wassenaar, J.; van Zutphen, S.; Mora, G.; Floch, L. P.; Siegler, M. A.; Spek, A. L.; Reek, J. N. H. Organometallics 2009, 28, 2724.

[57] Wassenaar, J.; Jansen, E.; van Zeist, W.-J.; Bickelhaupt, F. M.; Siegler, M. A.; Spek, A. L.; Reek, J. N. H. Nat. Chem. 2010, 2, 417.

[58] Shulyupin, M. O.; Franciò, G.; Beletskaya, I. P.; Leitner, W. Adv. Synth. Catal. 2005, 347, 667.

[59] Yu, S.-B.; Hu, X.-P.; Deng, J.; Wang, D.-Y.; Duan, Z.-C.; Zheng, Z. Tetrahedron: Asymmetry 2009, 20, 621.

[60] Boeda, F.; Rix, D.; Clavier, H.; Crévisy, C.; Mauduit, M. Tetrahedron: Asymmetry 2006, 17, 2726.

[61] Hou, C.-J.; Guo, W.-L.; Hu, X.-P.; Deng, J.; Zheng, Z. Tetrahedron: Asymmetry 2011, 22, 195.

[62] Hou, C.-J.; Wang, Y.-H.; Zheng, Z.; Xu, J.; Hu, X.-P. Org. Lett. 2012, 14, 3554.

[63] Blaser, H.-U.; Buser, H.-P.; Loers, K.; Hanreich, R.; Jalett, H. P.; Jelsch, E.; Pugin, B.; Schneider, H. D.; Spindler, F.; Wagmann, A. Chimia 1999, 53, 275. Blaser, H.-U.; Malan, C.; Pugin, B.; Spinder, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.

文章导航

/