综述与进展

铂催化α-酮酸酯不对称氢化反应的研究进展

  • 杨文 ,
  • 潘雪静 ,
  • 杨定乔
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  • 教育部环境理论化学重点实验室 华南师范大学化学与环境学院 广州 510006

收稿日期: 2014-11-07

  修回日期: 2015-01-21

  网络出版日期: 2015-02-10

基金资助

国家自然科学基金(Nos. 21172081, 21372090)、广东省自然科学基金重点(No. S2013020013091)和广州市科技计划(No. 156300018)资助项目.

Progress in Platinum-Catalyzed Asymmetric Hydrogenation of α-Keto Esters

  • Yang Wen ,
  • Pan Xuejing ,
  • Yang Dingqiao
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  • Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2014-11-07

  Revised date: 2015-01-21

  Online published: 2015-02-10

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172081, 21372090), the Natural Science Foundation of Guangdong Province (No. S2013020013091) and the City of Guangzhou Science and Technology Plan Projects (No. 156300018).

摘要

铂催化α-酮酸酯不对称氢化反应是合成手性α-羟基酯的重要方法之一. 综述了近年来铂催化α-酮酸酯不对称氢化多相反应的研究进展, 重点讨论了修饰型铂催化剂、负载型铂催化剂、纳米簇和胶体铂催化剂等不同种类铂催化剂对不对称氢化反应的影响, 并对可能的反应机理进行了讨论.

本文引用格式

杨文 , 潘雪静 , 杨定乔 . 铂催化α-酮酸酯不对称氢化反应的研究进展[J]. 有机化学, 2015 , 35(6) : 1216 -1228 . DOI: 10.6023/cjoc201411009

Abstract

Platinum-catalyzed enantioselective hydrogenation of α-keto esters is one of the most effective methods for the synthesis of chiral α-hydroxy esters. The recent progress in platinum-catalyzed heterogeneous asymmetric hydrogenation of α-keto esters is reviewed. It was paid great attention to the influences of modified platinum catalyst, supported platinum catalyst, nanoparticle platinum catalysts, and platinum colloids on the asymmetric hydrogenation. What’s more, the possible mechanisms are also discussed in this review.

参考文献

[1] Li, C.; Zhang, H.-D.; Jiang, D.-M.; Yang, Q.-H. Chem. Commun. 2007, 6, 547.
[2] Zhang, W.-C.; Zhang, X.-M. Angew. Chem., Int. Ed. 2006, 45, 5515.
[3] Liu, L.-Z.; Han, J.-C.; Yue, G.-Z.; Li, C.-C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 13608.
[4] Fujita, M.; Mori, K.; Shimogaki, M.; Sugimura, T. Org. Lett. 2012, 14, 1294.
[5] Mallat, T.; Orglmeister, E.; Baiker, A. Chem. Rev. 2007, 107, 4863.
[6] Baiker, A. J. Mol. Catal. A: Chem. 1997, 115, 473.
[7] Yang, C.-F.; Jiang, H.-Y.; Feng, J.; Fu, H.-Y.; Li, R.-X.; Chen, H.; Li, X.-J. J. Mol. Catal. A: Chem. 2009, 300, 98.
[8] Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713.
[9] Lavoie, S.; Laliberte, M. A.; Temprano, I.; McBreen, P. H. J. Am. Chem. Soc. 2006, 128, 7588.
[10] Baddeley, C. J. Top. Catal. 2003, 25, 17.
[11] Balázsik, K.; Bartók, M. J. Catal. 2004, 224, 463.
[12] Bürgi, T.; Baiker, A. Acc. Chem. Res. 2004, 37, 909.
[13] Zuo, X.-B.; Liu, H.-F. J. Mol. Catal. 1997, 11, 309 (in Chinese). (左晓斌, 刘汉范, 分子催化, 1997, 11, 309.)
[14] Orito, Y.; Imai, S.; Niwa, S. J. Chem. Soc. Jpn. 1979, 37, 173.
[15] Balázsik, K.; Szöri, K.; Felföldi, K.; Török, B.; Bartók, M. Chem. Commun. 2000, 7, 555.
[16] Diezi, S.; Reimann, S.; Bonalumi, N.; Mallat, T.; Baiker, A. J. Catal. 2006, 239, 255.
[17] Hoxha, F.; Königsmana, L.; Vargas, A.; Ferri, D.; Mallat, T.; Baiker, A. J. Am. Chem. Soc. 2007, 129, 10582.
[18] Diezi, S.; Szabo, A.; Mallat, A.; Baiker, A. J. Catal. 2004, 228, 162.
[19] Tao, G.-Z.; Lu, G.-Z.; Guo, Y.; Wang, Y.-Q.; Guo, Y.-L.; Zhang, Z.-G.; Liu, X.-H.; Wang, Y.-S. Chin. J. Catal. 2009, 30, 391 (in Chinese). (陶国忠, 卢冠忠, 郭 耘, 王艳芹, 郭杨龙, 张志刚, 刘晓晖, 王筠松, 催化学报, 2009, 30, 391.)
[20] Bartók, M.; Balázsik, K.; Notheisz, F. React. Kinet. Catal. Lett. 2002, 77, 363.
[21] Maeda, N.; Hungerbühler, K.; Baiker, A. J. Am. Chem. Soc. 2011, 133, 19567.
[22] Taskinen, A.; Nieminen, V.; Hotokka, M.; Murzin, D. Y. J. Phys. Chem. C 2007, 111, 5128.
[23] Meemken, F.;Maeda. N.; Hungerühler. K.; Baiker, A. Angew. Chem., Int. Ed. 2012, 51, 8212.
[24] Blaser, H. U.; Studer, M. Acc. Chem. Res. 2007, 40, 1348.
[25] Minder, B.; Mallat, T.; Baiker, A.; Wang, G.; Heinz, T.; Pfaltz, A. J. Catal. 1995, 154, 371.
[26] Wang, G.; Heinz, T.; Pfaltz, A.; Minder, B.; Mallat, T.; Baiker. A. J. Chem. Soc., Chem. Commun. 1994, 18, 2047.
[27] Simons, K. E.; Wang, G.; Heinz, T.; Giger, Y.; Mallat, T.; Pfaltz, A.; Baiker, A. Tetrahedron: Asymmetry 1995, 6, 505.
[28] Orglmeister, E.; Mallat, T.; Baiker, A. Adv. Synth. Catal. 2005, 347, 78.
[29] Goubert, G.; Demers-Carpentier, V.; Loach, R. P.; Lafleur-Lambert, R.; Lemay, J.-C.; Boukouvalas, J.; McBreen, P. H. ACS. Catal. 2013, 3, 2677.
[30] Meemken, F.; Steiger, T.; Holland, M. C.; Gilmour, R.; Hungerbühler, K.; Baiker, A. Catal. Sci. Technol. 2015, 5, 750.
[31] Marinas, A.; Mallat, T.; Baiker, A. J. Catal. 2004, 221, 666.
[32] Sutyinszki, M.; Szöri, K.; Felföldi, K.; Bartók, M. Catal. Commun. 2002, 3, 125.
[33] Azmat, M. U.; Guo, Y.; Guo, Y.; Wang, Y.-Q.; Lu, G.-Z. J. Mol. Catal. A: Chem. 2011, 336, 42.
[34] Fraga, M. A.; Mendes, M. J.; Jordão, E. J. Mol. Catal. A: Chem. 2002, 179, 243.
[35] Zhang, H.-D.; Xiang, S.; Li, C. Chem. Commun. 2005, 9, 1209.
[36] Davies, M. E. Nature 2002, 417, 813.
[37] Tong, Q.-F.; Shi, J.-L.; Song, Y.-Z.; Guo, Q.-G.; Liu, L. Carbon 2005, 43, 2013.
[38] Zuo, X.-B.; Liu, H.-F.; Liu, M.-H. Tetrahedron Lett. 1998, 39, 1941.
[39] Zuo, X.-B.; Liu, H.-F. Tetrahedron 1999, 55, 7787.
[40] Zhang, X.-Q.; He, N.-Z.; Xiao, M.-T.; Ye, J. Chem. Ind. Eng. Prog. 2013, 32, 2650 (in Chinese). (张学勤, 何年志, 肖美添, 叶 静, 化工进展, 2013, 32, 2650.)
[41] Kresge, C. T.; Leonowicz, M. E.; Roth, W. J.; Vartuli, J. C.; Beck, J. S. Nature 1992, 359, 710.
[42] Basu, S.; Mapa, M.; Gopinath, C. S.; Doble, M.; Bhaduri, S.; Lahiri, G. K. J. Catal. 2006, 239, 154.
[43] Xing, L.; Du, F.; Liang, J.-J.; Chen, Y.-S.; Zhou, Q.-L. J. Mol. Catal. A: Chem. 2007, 276, 191.
[44] Bhowmick, R.; Rajasekaran, S.; Friebel, D.; Beasley, C.; Jiao, L.; Ogasawara, H.; Dai, H. J.; Clemens, B.; Nilsson, A. J. Am. Chem. Soc. 2011, 133, 5580.
[45] Chen, Z.-J.; Guan, Z.-H.; Li, M.-G.; Yang, Q.-H.; Li, C. Angew. Chem., Int. Ed. 2011, 50, 4913.
[46] Li, X.-H.; Shen, Y.-L.; Xing, R.; Liu, Y.-M.; W, H.-H.; He, M.-Y.; Wu, P. Catal. Lett. 2008, 122, 325.
[47] Wang, H.-H.; Wang, H.-N.; Li, X.-H.; Wang, Y.-M.; Wu, P. Chin. J. Catal. 2011, 32, 1677.
[48] Wang, H.-N.; Li, X.-H.; Wang, Y.-M.; Wu, P. Chem. Catal. Chem. 2010, 2, 1303.
[49] Li, B.; Li, X.-H.; Wang, H.-N.; Wu, P. J. Mol. Catal. A: Chem. 2011, 345, 81.
[50] Li, B.; Li, X.-H.; Ding, Y.; Wu, P. Catal. Lett. 2012. 142. 1033.
[51] Li, Q.; Zhang, X.-Q.; Xiao, M.-T.; Liu, Y.-J. Catal. Commun. 2013. 42. 68.
[52] Zhang, X.-Q.; Li, Q.; Xiao, M.-T.; Liu, Y.-J. Appl. Catal. A: Gen. 2014, 480, 50.
[53] Pan, H.-Y.; Li, X.-H.; Zhang, D.-M.; Guan, Y.-J.; Wu, P. J. Mol. Catal. A: Chem. 2013, 377, 108.
[54] Beier. M.-J.; Andanson, J.-M.; Mallat, T.; Krumeich, F.; Baiker, A. ACS. Catal. 2012, 2, 337.
[55] Roucous, A.; Schulz, J.; Patin, H. Chem. Rev. 2002, 102, 3757.
[56] Margitfalvi, J. L.; Tálas, E.; Hegedüs, M. Chem. Commun. 1999, 7, 645.
[57] Wang, H.-J.; Wang, L.; Sato, T.; Sakamoto, Y.; Tominaka, S.; Miyasaka, K.; Miyamoto, N.; Nemoto, Y.; Terasaki, O.; Yamauchi, Y. Chem. Mater. 2012, 24, 1591.
[58] Bönnemann, H.; Gerhard, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1992.
[59] Jiang, P.; Li, X.-H.; Guan, Y.-J.; Ying, P.-L.; Li, C. J. Mol. Catal. 2004, 18, 381 (in Chinese). (姜鹏, 李晓红, 关亚军, 应品良, 李灿, 分子催化, 2004, 18, 381.)
[60] Weng, Z.-H.; Zaera, F. J. Phys. Chem. 2014, 118, 3672.
[61] Török, B.; Szöllösi, G.; Balázsik, K.; Felföldi, K.; Kun, I.; Bartók, M. Ultrason. Sonochem. 1999, 6, 97.
[62] Studer, M.; Blaser, H. U.; Exner, C. Adv. Synth. Catal. 2003, 345, 45.
[63] Perkas, N.; Rotter, H.; Vradman, L.; Landau, M. V.; Gedanken, A. Langmuir 2006, 22, 7072.
[64] Shanmugam, S.; Gedanken, A. J. Phys. Chem. C 2009, 113, 18707.
[65] Török, B.; Balázsik, K.; Szöllösi, G.; Felföldi, K.; Bartok, M. Chirality 1999, 11, 470.
[66] Müller, C.; Nijkamp, M. G.; Vogt, D. Eur. J. Inorg. Chem. 2005, 4011.
[67] Crooks, M. R.; Zhao, M.-Q.; Sun, L.; Chechik, V.; Yeunk. L. K. Acc. Chem. Res. 2001, 34, 181.
[68] Astruc, D.; Lu, F.; Aranzaes, J.-R. Angew. Chem., Int. Ed. 2005, 44, 7852.

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