Chinese Journal of Organic Chemistry >
Progress in Platinum-Catalyzed Asymmetric Hydrogenation of α-Keto Esters
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).
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.
Yang Wen , Pan Xuejing , Yang Dingqiao . Progress in Platinum-Catalyzed Asymmetric Hydrogenation of α-Keto Esters[J]. Chinese Journal of Organic Chemistry, 2015 , 35(6) : 1216 -1228 . DOI: 10.6023/cjoc201411009
[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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