SIOC 中文
ACS
Adv search

Acta Chimica Sinica >

2012 , Vol. 70 >Issue 13: 1427 - 1438

DOI: https://doi.org/10.6023/A12060268

Review

New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation

  • Xie Jianhua ,
  • Zhou Qilin
Expand
  • State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received date: 2012-06-02

  Online published: 2012-06-26

Supported by

Project supported by the National Natural Science Foundation of China, the National Basic Research Program of China (973 Program) (No. 2012CB821600), the “111” project (No. B06005) of the Ministry of Education of China.

Fold

Abstract

Chiral transition metal complexes-catalyzed asymmetric hydrogenation is one of the most efficient methods for the synthesis of optically active compounds, and has been intensively investigated in the past decades. This review presents a brief overview on the progress in the transition metal-catalyzed asymmetric hydrogenation since the beginning of this new century from three aspects: (1) chiral ligands and catalysts; (2) new catalytic asymmetric hydrogenations; (3) new methods and new strategies in asymmetric hydrogenations. Chiral monodentate phosphorus ligands have been a renaissance from the beginning of new century, and many efficient chiral monophosphoramidites such as MonoPhos, SiPhos, DpenPhos have been developed. The chiral phosphine ligands with a chirality on the phosphorus atom (P-chirality), such as BenzP*, ZhanPhos, and TriFer, have also been explored. Chiral ligands with a spiro skeleton have been a highlight of design and synthesis of chiral ligands. The chiral spiro ligands such as SDP, SiPhos, SIPHOX, and SpinPHOX are very efficient in asymmetric hydrogenations. The iridium complexes of chiral spiro pyridine-aminophosphine ligands SpiroPAP is the most efficient molecular catalysts up to now with a turnover number (ratio of converted substrate to catalyst) over 4500000 in the hydrogenation of acetophenone. A number of breakthroughs have been made in the researches on new catalytic asymmetric hydrogenations. Highly enantioslective hydrogenations of unprotected enamines, heteroaromatic compounds, and N-H imines have been developed. New methods and strategies including self-assembled, dendrimerized, and ferromagnetic nanomaterials-loaded chiral catalysts with recyclability and reusability, the catalysts with “mixed” chiral ligands have also been successfully applied in the catalytic asymmetric hydrogenations. However, the chiral transition metal complexes catalyzed asymmetric hydrogenation still has many challenges and is looking forward to new breakthroughs in the future. In addition to the continuous developments of new chiral ligands and catalysts with high efficiency, high enantioselectivity, and high chemoselectivity, new strategies such as co-operative or relay catalysis are becoming focuses of the asymmetric hydrogenations studies.

Key words： asymmetric hydrogenation; chiral ligands; chiral catalyst; chiral compounds; metal catalysts

Cite this article

Xie Jianhua , Zhou Qilin . New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation[J]. Acta Chimica Sinica, 2012 , 70(13) : 1427 -1438 . DOI: 10.6023/A12060268

References

[1] Guo, H.-C.; Ding, K.-L.; Dai, L.-X. Chin. Sci. Bull. 2004, 49, 1575. (郭红超, 丁奎岭, 戴立信, 科学通报, 2004, 49, 1575.)

[2] Guillen, F.; Fiaud, J.-C. Tetrahedron Lett. 1999, 40, 2939.

[3] Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Marorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 961.

[4] van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539.

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

[6] Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480.

[7] Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem. Int. Ed. 2002, 41, 2348.

[8] Huang, H.; Zheng, Z.; Luo, H.; Bai, C.; Hu, X.; Chen, H. J. Org. Chem. 2004, 69, 2355.

[9] Liu, Y.; Ding, K. J. Am. Chem. Soc. 2005, 127, 10488.

[10] (a) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713; (b) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.

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

[12] 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.

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

[14] Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H. Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.

[15] (a) Hoge, G.; Wu, H.-P.; Kissel, W. S.; Pflum, D. A.; Greene, D. J.; Bao, J. J. Am. Chem. Soc. 2004, 126, 5966; (b) Wu, H.-P.; Hoge, G. Org. Lett. 2004, 6, 3645.

[16] Tamura, K.; Sugiya, M.; Yoshida, K.; Yanagisawa, A.; Imamoto, T. Org. Lett. 2010, 12, 4400.

[17] Tang, W.; Capacci, A. G.; White, A.; Ma, S.; Rodriguez, S.; Qu, B.; Savoie, J.; Patel, N. D.; Wei, X.; Haddad, N.; Grinberg, N.; Yee, N. K.; Krishnamurthyl, D.; Senanayake, C. H. Org. Lett. 2010, 12, 1104.

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

[19] Chen, W.; McCormack, P. J.; Mohammed, K.; Mbafor, W.; Roberts, S. M.; Whittall, J. Angew. Chem. Int. Ed. 2007, 46, 4141.

[20] (a) Xie, J.-H.; Zhou, Q.-L. Acc. Chem. Res. 2008, 41, 581; (b) Ding, K.; Han, Z.; Wang, Z. Chem. Asian J. 2009, 4, 32.

[21] (a) Li, S.; Zhu, S.-F.; Zhang, C.-M.; Song, S.; Zhou, Q.-L. J. Am. Chem. Soc. 2008, 130, 8584; (b) Li, S.; Zhu, S.-F.; Xie, J.-H.; Zhang, C.-M.; Zhou, Q.-L. J. Am. Chem. Soc. 2010, 132, 1172.

[22] Han, Z.; Wang, Z.; Zhang, X.; Ding, K. Angew. Chem. Int. Ed. 2009, 48, 5345.

[23] Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.

[24] Sandoval, C.; Ohkuma, T.; Muñz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490.

[25] Blaser, H. U.; Buser, H. P.; Coers, K.; Hanreich,R.; Jalett, H. P.; Jelswch, E; Pugin, B.; Schneider, H. D.; Spindler, F.; Wegmann, A. Chimia, 1999, 53, 275.

[26] Xie, J.-H.; Liu, X.-Y.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem. Int. Ed. 2011, 50, 7329.

[27] Arai, N.; Ohkuma, T. Chem. Rec. 2012, 12, 284.

[28] Xie, J.-H.; Liu, X.-Y.; Yang, X.-H.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem. Int. Ed. 2012, 51, 201.

[29] Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. H. Angew. Chem. Int. Ed. 2008, 47, 940.

[30] Shimizu, H.; Igarashi, D.; Kuriyama, W.; Yusa, Y.; Sayo, N.; Saito, T. Org. Lett. 2007, 9, 1655.

[31] Monfette, S.; Turner, Z. R.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2012, 134, 4561.

[32] Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357.

[33] Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.

[34] Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.

[35] Lu, S.-M.; Wang, Y.-Q.; Han, X.-W.; Zhou, Y.-G. Angew. Chem. Int. Ed. 2006, 45, 2260.

[36] Wang, D.-S.; Chen, Q.-A.; Li, W.; Yu, C.-B.; Zhou, Y.-G.; Zhang, X.-M. J. Am. Chem. Soc. 2010, 132, 8909.

[37] Wang, D.-S.; Ye, Z.-S.; Chen, Q.-A.; Zhou, Y.-G.; Yu, C.-B.; Fan, H.-J.; Duan, Y. J. Am. Chem. Soc. 2011, 133, 8866.

[38] 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.

[39] Legualt, C. Y.; Charette, A. D. J. Am. Chem. Soc. 2005, 127, 8966.

[40] Kaiser, S.; Smidt, S. P.; Pfaltz, A. Angew. Chem. Int. Ed. 2006, 45, 5194.

[41] Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.

[42] Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D., III.; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918.

[43] Hansen, K. B.; Hsiao, Y.; Xu, F.; Rivera, N.; Clausen, A.; Kubryk, M.; Krska, S.; Rosner, T.; Simmons, B.; Balsells, J.; Ikemoto, N.; Sun, Y.; Spindler, F.; Malan, C.; Grabowski, E. J. J.; Armstrong, J. D., III. J. Am. Chem. Soc. 2009, 131, 8798.

[44] Hou, G.; Li, W.; Ma, M.; Zhang, X.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 12844.

[45] Hou, G.-H.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2006, 128, 11774.

[46] Hou, G.-H.; Xie, J.-H.; Yan, P.-C.; Zhou, Q.-L. J. Am. Chem. Soc. 2009, 131, 1366.

[47] Yan, P.-C.; Xie, J.-H.; Hou, G.-H.; Wang, L.-X.; Zhou, Q.-L. Adv. Synth. Catal. 2009, 351, 3243.

[48] Yan, P.-C.; Xie, J.-H.; Zhou, Q.-L. Chin. J. Chem. 2010, 28, 1736.

[49] Hou, G.; Gosselin, F.; Li, W.; McWilliams, C.; Sun, Y.; Weisel, M.; O’Shea, P. D.; Chen, C.-Y.; Davies, I. W.; Zhang, X. J. Am. Chem. Soc. 2009, 131, 9882.

[50] Hou, G.; Tao, R.; Sun, Y.; Zhang, X.; Gosselin, F. J. Am. Chem. Soc. 2010, 132, 2124.

[51] Bell, S.; Wüstenberg, B.; Kaiser, S.; Menges, F.; Netscher, T.; Pfaltz, A. Science 2006, 311, 642.

[52] Zhang, J.; Li, Y.; Wang, Z.; Ding, K. Angew. Chem. Int. Ed. 2011, 50, 11743.

[53] Wang, X.; Ding, K. J. Am. Chem. Soc. 2004, 126, 10524.

[54] Shi, L.; Wang, X.; Sandoval, C. A.; Li, M.; Qi, Q.; Li, Z.; Ding, K. Angew. Chem. Int. Ed. 2006, 45, 4108.

[55] Xu, L.; Wang, Z.; Wu, J.; Tu, S.; Ding, K. Angew. Chem. Int. Ed. 2010, 49, 3627.

[56] Liang, Y.; Jing, Q.; Li, X.; Ding, K. J. Am. Chem. Soc. 2005, 127, 7694.

[57] Hu, A.; Yee, G. T.; Lin, W. J. Am. Chem. Soc. 2005, 127, 12486.

[58] Wang, Z.-J.; Deng, G.-J.; Li, Y.; He, Y.-M.; Tang, W.-J.; Fan, Q.-H. Org. Lett. 2007, 9, 1243.

[59] Zhou, H.; Li, Z.; Wang, Z.; Wang, T.; Xu, L.; He, Y.; Fan, Q.-H.; Pan, J.; Gu, L.; Chan, A. S. C. Angew. Chem. Int. Ed. 2008, 47, 8464.

[60] Jäkel, C.; Paciello, R. Chem. Rev. 2006, 106, 1912.

[61] Reetz, M. T.; Sell, T.; Meiswinkel, A.; Mehler, G. Angew. Chem. Int. Ed. 2003, 42, 1433.

[62] Peña, D.; Minnaard, A. J.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Org. Biomol. Chem. 2003, 1, 1087.

[63] Hoen, R.; Boogers, J. A. F.; Bernsmann, H.; Minnaard, A. J.; Meetsma, A.; Tiemersma-Wegman, T. D.; de Vries, A. H. M.; de Vires, J. G.; Feringa, B. L. Angew. Chem. Int. Ed. 2005, 44, 4209.

[64] Boogers, J. A. F.; Felfer, U.; Kotthaus, M.; Lefort, L.; Steinbauer, G.; de Vries, A. H. M.; de Vries, J. G. Org. Proc. Res. Dev. 2007, 11, 585.

[65] Jiang, X.-B.; Lefort, L.; Goudriaan, P. E.; de Vires, A. H. M.; van Leeuwen, P. W. N. M.; de Vries, J. G.; Reek, J. N. H. Angew. Chem. Int. Ed. 2006, 45, 1223.

[66] Weis, M.; Waloch, C.; Seiche, W.; Breit, B. J. Am. Chem. Soc. 2006, 128, 4188.

[67] Wieland, J.; Breit, B. Nature Chem. 2010, 2, 832.

[68] Li, C.; Wang, C.; Villa-Marcos, B.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 14450.

[69] Li, C.; Villa-Marcos, B.; Xiao, J. J. Am. Chem. Soc. 2009, 131, 6967.

[70] Chen, Q.-A.; Wang, D.-S.; Zhou, Y.-G.; Duan, Y.; Fan, H.-J.; Yang, Y.; Zhang, Z. J. Am. Chem. Soc. 2011, 133, 6126.

[71] Chen, Q.-A.; Chen, M.-W.; Yu, C.-B.; Shi, L.; Wang, D.-S.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2011, 133, 16432.
Options
Outlines

/

〈 〉