Reviews

Recent Advance of Amino-acids and Their Derivatives as Chiral Ligands in Asymmetric Transfer Hydrogenation of Ketones

  • LI Xiao-Na ,
  • ZHANG Peng-Liang ,
  • DUAN Kai ,
  • WANG Jia-Xi
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  • School of Chemical Engineering, Hebei University of Technology, Tianjin 300130

Received date: 2011-04-23

  Revised date: 2011-06-10

  Online published: 2011-08-24

Supported by

Project supported by the Natural Science Foundation of Hebei Province (No. B2011202087).

Abstract

The asymmetric transfer hydrogenation (ATH) reaction of prochiral ketones is an important method to produce chiral alcohols. Recently, the application of chiral amino acids and their derivatives as ligands in ATH of prochiral ketones promoted by the ruthenium, rhodium or iridium complexes have been attracted more attentions. Herein the catalytic properties of amino acids, amino acid based amides, thioamides, hydroxamic acids, hydrazides, amino alcohols and hydroxy amides as ligands in the ruthenium, rhodium or iridium catalyzed ATH of prochiral ketones have been overviewed.

Cite this article

LI Xiao-Na , ZHANG Peng-Liang , DUAN Kai , WANG Jia-Xi . Recent Advance of Amino-acids and Their Derivatives as Chiral Ligands in Asymmetric Transfer Hydrogenation of Ketones[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 19 -29 . DOI: 10.6023/cjoc1104231

References

[1] Ma, G.; Medonald, R.; Ferguson, M.; Cavell, R. G.; Patrick, B. O.; James, B. R.; Hu, T. Q. Organometallics 2007, 26, 846.

[2] Malacea, R.; Poli, R.; Manoury, E. Coord. Chem. Rev. 2010, 254, 729.

[3] Cui, J.-G.; Yan, R.-A.; Zeng, H.-M. Chin J. Org. Chem. 1998, 18, 521 (in Chinese). (崔建国, 晏日安, 曾陇梅, 有机化学, 1998, 18, 521.)

[4] Gladali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226.

[5] Liu, Y.-H.; Liu, X.-L.; Yuan, D.-M.; Shi, Y.-C.; Jing, X.-B.; Wu, J. Chin. J. Org. Chem. 2005, 28, 893 (in Chinese). (刘永红, 刘晓岚, 袁冬梅, 石尧成, 景淆壁, 吴俊, 有机化学, 2005, 28, 893.)

[6] Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.

[7] Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.

[8] Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045.

[9] Wang, C.; Wu, X. F.; Xiao, J. L. Chem. Asian J. 2008, 3, 1750.

[10] Mori, A.; Abe, H.; Inoue, S. Appl. Organomet. Chem. 1995, 9, 189.

[11] Severin, K.; Bergs, R.; Beck, W. Angew. Chem., Int. Ed. 1998, 37, 1634.

[12] Paradowska, J.; Stodulski, M.; Mlynarski, J. Angew. Chem., Int. Ed. 2009, 48, 4288.

[13] Carter, L. C.; Davies, D. L.; Duffy, K. T.; Fawcett, J.; Russell, D. R. Acta Crystallogr. 1994, C50, 1559.

[14] Ohta, T.; Nakahara, S. I.; Shigemura, Y.; Hattori, K.; Furukawa, I. Chem. Lett. 1998, 491.

[15] Carmona, D.; Lamata, M. P.; Viguri, F.; Dobrinovich, I.; Lahoz, F. J.; Oroa, L. A. Adv. Synth. Catal. 2002, 344, 499.

[16] Carmona, D.; Lamata, M. P.; Oro, L. A. Eur. J. Inorg. Chem. 2002, 2239.

[17] Carmona, D.; Lahoz, F. J.; Atencio, R.; Oro, L. A.; Lamata, M. P.; Viguri, F.; José, E. S.; Vega, C.; Reyes, J.; Joó, F.; Kathó, Â. Chem. Eur. J. 1999, 5, 1544.

[18] Ohta, T.; Nakahara, S. I.; Shigemura, Y.; Hattori, K.; Furukawa, I. Appl. Organomet. Chem. 2001, 15, 699.

[19] Kathó, Â.; Carmona, D.; Viguri, F.; Remacha, C. D.; Kovács, J.; Joó, F.; Oro, L. A. J. Organomet. Chem. 2000, 593~594, 299.

[20] Faller, J. W.; Lavoie, A. R. Organometallics 2001, 20, 5245.

[21] Ahlford, K.; Adolfsson, H. Catal. Commun. 2011, 12, 1118.

[22] Bacchi, A.; Pelagatt, P.; Pelizzi, C.; Rogolino, D. J. Organomet. Chem. 2009, 694, 3200.

[23] Rhyoo, H. Y.; Yoon, Y. A.; Park, H. J.; Chung, Y. K. Tetrahedron Lett. 2001, 42, 5045.

[24] Rhyoo, H. Y.; Park, H. J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269.

[25] Rhyoo, H. Y.; Park, H. J.; Chung, Y. K. Chem. Commun. 2001, 2064.

[26] Zeror, S.; Collin, J.; Fiaud, J. C.; Zouioueche, L. A. J. Mol. Catal. A: Chem. 2006, 256, 85.

[27] Mao, J. C.; Guo, J. Chirality 2010, 22, 173.

[28] Zeror, S.; Collin, J.; Fiaud, J. C.; Zouioueche, L. A. Adv. Synth. Catal. 2008, 350, 197.

[29] Zhou, Z. Q.; Wu, L. H. Catal. Commun. 2008, 9, 2539.

[30] Pelagatti, P.; Bacchi, A.; Calbiani, F.; Carcelli, M.; Elviri, L.; Pelizzi, C.; Rogolino, D. J. Organomet. Chem. 2005, 690, 4602.

[31] Pelagatti, P.; Carcelli, M.; Calbiani, F.; Cassi, C.; Elviri, L.; Pelizzi, L.; Rizzotti, U.; Rogolino, D. Organometallics 2005, 24, 5836.

[32] Zaitsev, A. B.; Adolfsson, H. Org. Lett. 2006, 8, 5129.

[33] Ahlford, K.; Livendahl, M.; Adolfsson, H. Tetrahedron Lett. 2009, 50, 6321.

[34] Ahlford, K.; Ekström, J.; Zaitsev, A. B.; Ryberg, P.; Eriksson, L.; Adolfsson, H. Chem. Eur. J. 2009, 15, 11197.

[35] Tinnis, F.; Adolfsson, H. Org. Biomol. Chem. 2010, 8, 4536.

[36] Ahlford, K.; Zaitsev, A. B.; Ekström, J.; Adolfsson, H. Synlett 2007, 2541.

[37] Wen, W.; Zhou, H.-Y.; Fu, H.-X.; Lü, S.-J. Chin J. Org. Chem. 1998, 18, 509 (in Chinese). (翁文, 周宏英, 傅宏祥, 吕士杰, 有机化学, 1998, 18, 509.)

[38] Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.

[39] Mao, J. C.; Wan, B. S.; Wu, F.; Lu, S. W. Tetrahedron Lett. 2005, 46, 7341.

[40] Everaere, K.; Mortreux, A.; Bulliard, M.; Brussee, J.; Gen, A.; Nowogrocki, G.; Carpentier, J. F. Eur. J. Org. Chem. 2001, 275.

[41] Petra, D. G. I.; Reek, J. N. H.; Handgraaf, J. W.; Meijer, E. J.; Dierkes, P.; Kamer, P. C. J.; Brussee, J.; Schoemaker, H. E.; Leeuwen, P. W. N. M. V. Chem. Eur. J. 2000, 6, 2818.

[42] Wu, X. F.; Li, X. H.; McConville, M.; Saidi, O.; Xiao, J. L. J. Mol. Catal. A: Chem. 2006, 247, 153.

[43] Pastor, I. M.; Vastila, P.; Adolfsson, H. Chem. Commun. 2002, 2046.

[44] Bøgevig, A.; Pastor, I. M.; Adolfsson, H. Chem. Eur. J. 2004, 10, 294.

[45] Pastor, I. M.; Vastila, P.; Adolfsson, H. Chem. Eur. J. 2003, 9, 4031.

[46] Vastila, P.; Wettergren, J.; Adolfsson, H. Chem. Commun. 2005, 4039.

[47] Wettergren, J.; Bøgevig, A.; Portier, M.; Adolfssona, H. Adv. Synth. Catal. 2006, 348, 1277.

[48] Lundberg, H.; Adolfsson, H. Tetrahedron Lett. 2011, 52, 2754.

[49] Vastila, P.; Zaitsev, A. B.; Wettergren, J.; Privalov, T.; Adolfsson, H. Chem. Eur. J. 2006, 12, 3218.

[50] Wettergren, J.; Buitrago, E.; Ryberg, P.; Adolfsson, H. Chem. Eur. J. 2009, 15, 5709.

[51] Yim, A. S. Y.; Wills, M. Tetrahedron 2005, 61, 7994.

[52] Wettergren, J.; Zaitsev, A. B.; Adolfsson, H. Adv. Synth. Catal. 2007, 349, 2556.

[53] Watts, C. C.; Thoniyot, P.; Cappuccio, F.; Verhagen, J.; Gallagher, B.; Singaram, B. Tetrahedron: Asymmetry 2006, 17, 1301.

[54] Geoghegan, P.; O'Leary, P. Tetrahedron: Asymmetry 2010, 21, 867.

[55] McManus, H. A.; Barry, S. M.; Andersson, P. G.; Guiry, P. J. Tetrahedron 2004, 60, 3405.

[56] Aitali, M.; Allaoud, S.; Karim, A.; Meliet, C.; Mortreux, A. Tetrahedron: Asymmetry 2000, 11, 1367.

[57] Cambeiroa, X. C.; Pericàs, M. A. Adv. Synth. Catal. 2011, 353, 113.

[58] Zani, L.; Eriksson, L.; Adolfsson, H. Eur. J. Org. Chem. 2008, 4655.
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