Citation:
Yuan Qianjia, Zhang Wanbin. Applications of Phosphoramidite Ligands in Ir-Catalyzed Asymmetric Hydrogenation Reactions[J]. Chinese Journal of Organic Chemistry,
;2016, 36(2): 274-282.
doi:
10.6023/cjoc201509016
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Phosphoramidites, as a class of privileged chiral ligands, are suitable for different types of reactions, such as catalytic asymmetric hydrogenation, catalytic asymmetric allylic substitution, catalytic asymmetric Diels-Alder reaction and so on. Catalytic asymmetric hydrogenation reactions are some of the most important reactions in industry. In this review recent advances and applications of phosphoramidite ligands in Ir-catalyzed asymmetric hydrogenation of enamides and their derivatives, unfunctionalized enamines, imines and heteroaromatic compounds are discussed.
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-
[1]
[1] (a) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008. (b) Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Chin. J. Org. Chem. 2005, 25, 634 (in Chinese). (卢胜梅, 韩秀文, 周永贵, 有机化学, 2005, 25, 634.) (c) de Vries, J. G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, 2007. (d) Ma, Y.-H.; Zhang, Y.-J.; Zhang, W. Chin. J. Org. Chem. 2007, 27, 289 (in Chinese). (马元辉, 张勇健, 张万斌, 有机化学, 2007, 27, 289.) (e) Blaser, H. U.; Federsel. H.-J. Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, 2nd ed., Wiley-VCH, Weinheim, 2010. (f) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713.
-
[2]
[2] (a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (b) Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258. (c) Zhang, W.; Liu, D. In Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications, Chapter 7, Wiley-VCH, Weinheim, 2010. (d) Kazmaier, U. Transition Meatl Catalyzed Enantioselective Allylic Substitution in Organic Synthesis, Springer: New York, 2012. (e) Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
-
[3]
[3] (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. (b) Kobayashi, S.; Jorgenson, K. A. Cycloaddition Reaction in Organic Synthesis, New York, Wiley-VCH, 2002. (c) Desimoni, G.; Faita, G.; Jorgenson, K. A. Chem. Rev. 2006, 106, 3561.
-
[4]
[4] (a) Porter, M. J.; Skidmore, J. Chem. Commun. 2000, 36, 1215. (b) Xia, Q.-H.; Ge, H.-Q.; Ye, C.-P.; Liu, Z.-M.; Su, K.-X. Chem. Rev. 2005, 105, 1603.
-
[5]
[5] (a) RajanBabu, T. V. Chem. Rev. 2003, 103, 2845. (b) Jia, X.; Wang, Z.; Xia, C.; Ding, K. C. Chin. J. Org. Chem. 2013, 33, 1369 (in Chinese) (贾肖飞, 王正, 夏春谷, 丁奎岭, 有机化学, 2013, 33, 1369.)
-
[6]
[6] (a) Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691. (b) Teichert, J. F.; Feringa, B. L. Angew. Chem., Int. Ed. 2010, 49, 2486. (c) Zhang, Z.; Xie, F.; Yang, B.; Yu, H.; Zhang, W. Chin. J. Org. Chem. 2011, 31, 429 (in Chinese). (张振锋, 谢芳, 杨波, 余焓, 张万斌, 有机化学, 2011, 31, 429.) (d) Zhou, Q.-L. Privileged Chiral Ligands and Catalysts, Wiley- VCH: Weinheim, 2011.
-
[7]
[7] Hulst, R.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 699.
-
[8]
[8] de Veris, A. H. M.; Meetsma, A.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374.
-
[9]
[9] (a) Zhang, H.; Fang, F.; Xie, F.; Yu, H.; Yang, G.; Zhang, W. Tetrahedron Lett. 2010, 51, 3119. (b) Yang, B.; Xie, F.; Yu, H.; Shen, K.; Ma, Z.; Zhang, W. Tetrahedron 2011, 67, 6197. (c) Yu, H.; Xie, F.; Ma, Z.; Liu, Y.; Zhang, W. Org. Biomol. Chem. 2012, 10, 5137. (d) Yu, H.; Xie, F.; Ma, Z.; Liu, Y.; Zhang, W. Adv. Synth. Catal. 2012, 354, 1941.
-
[10]
[10] (a) Minnaard, A. J.; Feringa, B. L.; Lefort, L.; de Vries, J. G. Acc. Chem. Res. 2007, 40, 1267. (b) de Vries, A. H. M.; de Vries, J. G. Platinum Metals Rev. 2006, 50, 54.
-
[11]
[11] Giacomina, F.; Meetsma, A.; Panella, L.; Lefort, L.; de Vries, A. H. M.; de Vries, J. G. Angew. Chem., Int. Ed. 2007, 46, 1497.
-
[12]
[12] (a) Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402. (b) Zhang, J.; Yang, D.; Long, Y. Chin. J. Org. Chem. 2009, 29, 835 (in Chinese). (张俊芳, 杨定乔, 龙玉华, 有机化学, 2009, 29, 835.)
-
[13]
[13] Marie, P.; Deblon, S.; Breher, F.; Geier, J.; Böhler, C.; Rüegger, H.; Schönberg, H.; Grützmacher, H. Chem. Eur. J. 2004, 10, 4198.
-
[14]
[14] Broady, S. D.; Martin, D. M. G.; Lennon, I. C.; Ramsden, J. A.; Muir, J. C. WO 2006067412, 2006 [Chem. Abstr. 2006, 145, 103874].
-
[15]
[15] Erre, G.; Enthaler, S.; Junge, K.; Addis, D.; Beller, M. Adv. Synth. Catal. 2009, 351, 1437.
-
[16]
[16] Erre, G.; Junge, K.; Enthaler, S; Addis, D.; Michalik, D.; Spannenberg, A.; Beller, M. Chem. Asian J. 2008, 3, 887.
-
[17]
[17] Enthaler, S.; Erre, G.; Junge, K.; Schröder, K.; Addis, D.; Michalik, D.; Hapke, M.; Redkin, D.; Beller, M. Eur. J. Org. Chem. 2008, 3352.
-
[18]
[18] Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
-
[19]
[19] Hou, G.-H.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2006, 128, 11774.
-
[20]
[20] Hou, G.-H.; Xie, J.-H.; Yan, P.-C.; Zhou, Q.-L. J. Am. Chem. Soc. 2009, 131, 1366.
-
[21]
[21] Yan, P.-C.; Xie, J.-H.; Hou, G.-H.; Wang, L.-X.; Zhou, Q.-L. Adv. Synth. Catal. 2009, 351, 3243.
-
[22]
[22] Yan, P.-C.; Xie, J.-H.; Zhou, Q.-L. Chin. J. Chem. 2010, 28, 1736.
-
[23]
[23] (a) Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425. (b) Wang, D.-W.; Wang, X.-B.; Wang, D.-S.; Lu, S.-M.; Zhou, Y.-G.; Li, Y.-X. J. Org. Chem. 2009, 74, 2780.
-
[24]
[24] Blaser, H. U.; Buser, H. P.; Losers, K.; Hanreich, R.; Jalett, H. P.; Jelsch, E.; Pugin, B.; Schneider, H. D.; Splinder, F.; Wagmann, A. Chimia 1999, 53, 275.
-
[25]
[25] Mršić, N.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. J. Am. Chem. Soc. 2009, 131, 8358.
-
[26]
[26] Hou, G.; Tao, R.; Sun, Y.; Zhang, X.; Gosselin, F. J. Am. Chem. Soc. 2010, 132, 2124.
-
[27]
[27] Xie, J.-H.; Yan, P.-C.; Zhang, Q.-Q.; Yuan, K.-X.; Zhou, Q.-L. ACS Catal. 2012, 2, 561.
-
[28]
[28] 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.
-
[29]
[29] Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2011, 112, 2557.
-
[30]
[30] Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.
-
[31]
[31] Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Adv. Synth. Catal. 2004, 346, 909.
-
[32]
[32] Lam, K. H.; Lu, L.; Feng, L.; Fan, Q.-H.; Lam, F. L.; Lo, W.-H.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 1755.
-
[33]
[33] Reetz, M. T.; Li, X. Chem. Commun. 2006, 42, 2159.
-
[34]
[34] Wang, D.-W.; Zeng, W; Zhou, Y.-G. Tetrahedron: Asymmetry 2007, 18, 1103.
-
[35]
[35] Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
-
[36]
[36] Mršić, N.; Lefort, L.; Boogers, J. A. F.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Adv. Synth. Catal. 2008, 350, 1081.
-
[37]
[37] Mršić, N.; Jerphagnon, T.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Adv. Synth. Catal. 2009, 351, 2549.
-
[38]
[38] (a) Eggenstein, M.; Thomas, A.; Theuerkauf, J.; Franciò, G.; Leitner, W. Adv. Synth. Catal. 2009, 351, 725. (b) Hou, C.-J.; Wang, Y.-H.; Zheng, Z.; Xu, J.; Hu, X.-P. Org. Lett. 2012, 14, 3554.
-
[39]
[39] (a) Bess, E. N.; Sigman, M. S. Org. Lett. 2013, 15, 646. (b) Biosca, M.; Paptchikhine, A.; Pàmies, O.; Andersson, P. G.; Diéguez, M. Chem. Eur. J. 2015, 21, 3455.
-
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