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DOI: 10.1055/s-0033-1339479
Recent Advances in Metal-Catalyzed Asymmetric Mannich Reactions
Publication History
Received: 25 April 2013
Accepted after revision: 12 June 2013
Publication Date:
17 September 2013 (online)
Abstract
In this review, recent works on metal-catalyzed asymmetric Mannich, aza-Henry and vinylogous Mannich reactions are described. The asymmetric Mannich reaction is one of the most powerful methodologies among the carbon–carbon bond-forming reactions, and provides direct access to a wide range of optically active natural products with useful biological properties.
1 Introduction
2 Catalytic Asymmetric Mannich Reactions
2.1 BINOL Ligands
2.2 BINAP Ligands
2.3 Bisoxazoline Ligands
2.4 Pyridine Bisoxazoline Ligands
2.5 Diamine Ligands
2.6 P,N-Ligands
2.7 P,S-Ligands
2.8 P,P-Ligands
2.9 N,N-Ligands
2.10 Miscellaneous
3 Asymmetric Aza-Henry Reactions
3.1 BINOL Ligands
3.2 Bisoxazoline Ligands
3.3 N,N-Ligands
3.4 Miscellaneous
4 Asymmetric Vinylogous Mannich Reactions
5 Conclusion
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References
- 1 Chen Y, Yekta S, Yudin AK. Chem. Rev. 2003; 103: 3155
- 2 Brunel JM. Chem. Rev. 2005; 105: 857
- 3 Hatano M, Ishihara K. Synthesis 2010; 3785
- 4 Ishihara K, Miyata M, Hattori K, Tada T, Yamamoto H. J. Am. Chem. Soc. 1994; 116: 10520
- 5 Ishitani H, Ueno M, Kobayashi S. J. Am. Chem. Soc. 2000; 122: 8180
- 6 Kobayashi S, Ueno M, Saito S, Mizuki Y, Ishitani H, Yamashita Y. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5476
- 7 Kobayashi S, Ishitani H, Yamashita Y, Ueno M, Shimizu H. Tetrahedron 2001; 57: 861
- 8 Kobayashi S, Salter MM, Yamazaki Y, Yamashita Y. Chem. Asian J. 2010; 5: 493
- 9 Saruhashi K, Kobayashi S. J. Am. Chem. Soc. 2006; 128: 11232
- 10 Matsunaga S, Kumagai N, Harada S, Shibasaki M. J. Am. Chem. Soc. 2003; 125: 4712
- 11 Matsunaga S, Yoshida T, Morimoto H, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2004; 126: 8777
- 12 Sugita M, Yamaguchi A, Yamagiwa N, Handa S, Matsunaga S, Shibasaki M. Org. Lett. 2005; 7: 5339
- 13 Matsunaga S, Sugita M, Yamagiwa N, Handa S, Yamaguchi A, Shibasaki M. Bull. Chem. Soc. Jpn. 2006; 79: 1906
- 14 Yamaguchi A, Matsunaga S, Shibasaki M. Tetrahedron Lett. 2006; 47: 3985
- 15 Jaber N, Carrée F, Fiaud J-C, Collin J. Tetrahedron: Asymmetry 2003; 14: 2067
- 16 Harada S, Handa S, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2005; 44: 4365 ; Angew. Chem. 2005, 117, 4439
- 17 Yoshida T, Morimoto H, Kumagai N, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2005; 44: 3470; Angew. Chem. 2005, 117, 3536
- 18 Ihori Y, Yamashita Y, Ishitani H, Kobayashi S. J. Am. Chem. Soc. 2005; 127: 15528
- 19 Kobayashi S, Yazaki R, Seki K, Ueno M. Tetrahedron 2007; 63: 8425
- 20 Hatano M, Horibe T, Ishihara K. J. Am. Chem. Soc. 2010; 132: 56
- 21 Hatano M, Horibe T, Ishihara K. Org. Lett. 2010; 12: 3502
- 22 Hatano M, Moriyama K, Maki T, Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 3823 ; Angew. Chem. 2010, 122, 3911
- 23 Xu X, Qian Y, Yang L, Hu W. Chem. Commun. 2011; 47: 797
- 24 Lu G, Yoshino T, Morimoto H, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2011; 50: 4382 ; Angew. Chem. 2011, 123, 4474
- 25 Kato S, Yoshino T, Shibasaki M, Kanai M, Matsunaga S. Angew. Chem. Int. Ed. 2012; 51: 7007 ; Angew. Chem. 2012, 124, 7113
- 26 Miyashita A, Yasuda A, Takaya H, Toriumi K, Ito T, Souchi T, Noyori R. J. Am. Chem. Soc. 1980; 102: 7932
- 27 Woodward G, Berthod M, Mignani G, Lemaire M. Chem. Rev. 2005; 105: 1801
- 28 Ferraris D, Young B, Cox C, Dudding T, Drury III WJ, Ryzhkov L, Taggi AE, Lectka T. J. Am. Chem. Soc. 2002; 124: 67
- 29 Hamashima Y, Sasamoto N, Hotta D, Somei H, Umebayashi N, Sodeoka M. Angew. Chem. Int. Ed. 2005; 44: 1525 ; Angew. Chem. 2005, 117, 1549
- 30 Kim EJ, Kang YK, Kim DY. Bull. Korean Chem. Soc. 2009; 30: 1437
- 31 Desimoni G, Faita G, Jørgensen KA. Chem. Rev. 2006; 106: 3561
- 32 Rechavi D, Lemaire M. Chem. Rev. 2002; 102: 3467
- 33 Juhl K, Gathergood N, Jørgensen KA. Angew. Chem. Int. Ed. 2001; 40: 2995 ; Angew. Chem. 2001, 113, 3083
- 34 Marigo M, Kjærsgaard A, Juhl K, Gathergood N, Jørgensen KA. Chem. Eur. J. 2003; 9: 2359
- 35 Cutting GA, Stainforth NE, John MP, Kociok-Köhn G, Willis MC. J. Am. Chem. Soc. 2007; 129: 10632
- 36 Nakamura S, Sano H, Nakashima H, Kubo K, Shibata N, Toru T. Tetrahedron Lett. 2007; 48: 5565
- 37 Karimi B, Maleki A. Chem. Commun. 2009; 5180
- 38 Nishiyama H, Sakaguchi H, Nakamura T, Horihata M, Kondo M, Ito K. Organometallics 1989; 8: 846
- 39 Morimoto H, Lu G, Aoyama N, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2007; 129: 9588
- 40 Lu G, Morimoto H, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2008; 47: 6847 ; Angew. Chem. 2008, 120, 6953
- 41 Yamaguchi A, Matsunaga S, Shibasaki M. Org. Lett. 2008; 10: 2319
- 42 Poisson T, Tsubogo T, Yamashita Y, Kobayashi S. J. Org. Chem. 2010; 75: 963
- 43 Karimi B, Enders D, Jafari E. Chem. Eur. J. 2013; 19: 10142
- 44 Ueno M, Kitagawa H, Ishitani H, Yasuda S, Hanada K, Kobayashi S. Tetrahedron Lett. 2001; 42: 7863
- 45 Kobayashi S, Matsubara R, Kitagawa H. Org. Lett. 2002; 4: 143
- 46 Kobayashi S, Hamada T, Manabe K. J. Am. Chem. Soc. 2002; 124: 5640
- 47 Hamada T, Manabe K, Kobayashi S. J. Am. Chem. Soc. 2004; 126: 7768
- 48 Hamada T, Manabe K, Kobayashi S. Chem. Eur. J. 2006; 12: 1205
- 49 Bernardi L, Gothelf AS, Hazell RG, Jørgensen KA. J. Org. Chem. 2003; 68: 2583
- 50 Josephsohn NS, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2004; 126: 3734
- 51 Josephsohn NS, Carswell EL, Snapper ML, Hoveyda AH. Org. Lett. 2005; 7: 2711
- 52 Yan X.-X, Peng Q, Li Q, Zhang K, Yao J, Hou X.-L, Wu Y.-D. J. Am. Chem. Soc. 2008; 130: 14362
- 53 Chen Q.-A, Zeng W, Wang D.-W, Zhou Y.-G. Synlett 2009; 2236
- 54 Guo S, Xie Y, Hu X, Xia C, Huang H. Angew. Chem. Int. Ed. 2010; 49: 2728 ; Angew. Chem. 2010, 122, 2788
- 55 Liang G, Tong MC, Tao H, Wang CJ. Adv. Synth. Catal. 2010; 352: 1851
- 56 Yuan Z, Mei L, Wei Y, Shi M, Kattamuri P, McDowell P, Li G. Org. Biomol. Chem. 2012; 10: 2509
- 57 González AS, Arrayás RG, Carretero JC. Org. Lett. 2006; 8: 2977
- 58 Hernández-Toribio J, Arrayás RG, Carretero JC. J. Am. Chem. Soc. 2008; 130: 16150
- 59 Hernández-Toribio J, Arrayás RG, Carretero JC. Chem. Eur. J. 2010; 16: 1153
- 60 Imae K, Shimizu K, Ogata K, Fukuzawa S.-I. J. Org. Chem. 2011; 76: 3604
- 61 Sasamoto N, Dubs C, Hamashima Y, Sodeoka M. J. Am. Chem. Soc. 2006; 128: 14010
- 62 Dubs C, Hamashima Y, Sasamoto N, Seidel TM, Suzuki S, Hashizume D, Sodeoka M. J. Org. Chem. 2008; 73: 5859
- 63 Hamashima Y, Sasamoto N, Umebayashi N, Sodeoka M. Chem. Asian J. 2008; 3: 1443
- 64 Suto Y, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2007; 129: 500
- 65 Du Y, Xu L.-W, Shimizu Y, Oisaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2008; 130: 16146
- 66 Yin L, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 9610
- 67 Yin L, Kanai M, Shibasaki M. Tetrahedron 2012; 68: 3497
- 68 Suzuki Y, Yazaki R, Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2009; 48: 5026 ; Angew. Chem. 2009, 121, 5126
- 69 Kang YK, Kim D. Tetrahedron Lett. 2011; 52: 2356
- 70 Shang D, Liu Y, Zhou X, Liu X, Feng X. Chem. Eur. J. 2009; 15: 3678
- 71 Chen S, Hou Z, Zhu Y, Wang J, Lin L, Liu X, Feng X. Chem. Eur. J. 2009; 15: 5884
- 72 Xue S, Yu S, Deng Y, Wulff WD. Angew. Chem. Int. Ed. 2001; 40: 2271 ; Angew. Chem. 2001, 113, 2331
- 73 Trost BM, Terrell LR. J. Am. Chem. Soc. 2003; 125: 338
- 74 Trost BM, Jaratjaroonphong J, Reutrakul V. J. Am. Chem. Soc. 2006; 128: 2778
- 75 Xu Y, Lu G, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2009; 48: 3353 ; Angew. Chem. 2009, 121, 3403
- 76 Chen Z, Yakura K, Matsunaga S, Shibasaki M. Org. Lett. 2008; 10: 3239
- 77 Izumiseki A, Yoshida K, Yanagisawa A. Org. Lett. 2009; 11: 5310
- 78 Galeštoková Z, Šebesta R. Eur. J. Org. Chem. 2011; 7092
- 79 Adams H, Anderson JC, Peace S, Pennell AM. K. J. Org. Chem. 1998; 63: 9932
- 80 Li Z, Li C.-J. J. Am. Chem. Soc. 2005; 127: 3672
- 81 Bernardi L, Bonini BF, Capitó E, Dessole G, Comes-Franchini M, Fochi M, Ricci A. J. Org. Chem. 2004; 69: 8168
- 82 Westermann B. Angew. Chem. Int. Ed. 2003; 42: 151 ; Angew. Chem. 2003, 115, 161
- 83 Ting A, Schaus SE. Eur. J. Org. Chem. 2007; 5797
- 84 Henry L. Bull. Cl. Sci., Acad. R. Belg. 1896; 32: 33
- 85 Lucet D, Le Gall T, Mioskowski C. Angew. Chem. Int. Ed. 1998; 37: 2580 ; Angew. Chem. 1998, 110, 2724
- 86 Michalson ET, Szmuszkovicz J. Prog. Drug Res. 1989; 33: 135
- 87 Yamada K.-I, Harwood SJ, Gröger H, Shibasaki M. Angew. Chem. Int. Ed. 1999; 38: 3504 ; Angew. Chem. 1999, 111, 3713
- 88 Yamada K.-I, Moll G, Shibasaki M. Synlett 2001; 980
- 89 Knudsen KR, Risgaard T, Nishiwaki N, Gothelf KV, Jørgensen KA. J. Am. Chem. Soc. 2001; 123: 5843
- 90 Nishiwaki N, Knudsen KR, Gothelf KV, Jørgensen KA. Angew. Chem. Int. Ed. 2001; 40: 2992 ; Angew. Chem. 2001, 113, 3080
- 91 Knudsen KR, Jørgensen KA. Org. Biomol. Chem. 2005; 3: 1362
- 92 Anderson JC, Howell GP, Lawrence RM, Wilson C. J. Org. Chem. 2005; 70: 5665
- 93 Anderson JC, Blake AJ, Howell GP, Wilson C. J. Org. Chem. 2005; 70: 549
- 94 Lee A, Kim W, Lee J, Hyeon T, Kim BM. Tetrahedron: Asymmetry 2004; 15: 2595
- 95 Zhou H, Peng D, Qin B, Hou Z, Liu X, Feng X. J. Org. Chem. 2007; 72: 10302
- 96 Tan C, Liu X, Wang L, Wang J, Feng X. Org. Lett. 2008; 10: 5305
- 97 Palomo C, Oiarbide M, Halder R, Laso A, Lopez R. Angew. Chem. Int. Ed. 2006; 45: 117 ; Angew. Chem. 2006, 118, 123
- 98 Gao F, Zho J, Tang Y, Deng M, Qian C. Chirality 2006; 18: 741
- 99 Trost BM, Lupton DW. Org. Lett. 2007; 9: 2023
- 100 Handa S, Gnanadesikan V, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2007; 129: 4900
- 101 Handa S, Gnanadesikan V, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 4925
- 102 Chen Z, Morimoto H, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2008; 130: 2170
- 103 Zhang G, Yashima E, Woggon W.-D. Adv. Synth. Catal. 2009; 351: 1255
- 104 Nitabaru T, Kumagai N, Shibasaki M. Molecules 2010; 15: 1280
- 105 Casiraghi G, Zanardi F, Battistini L, Rassu G. Synlett 2009; 1525
- 106 Casiraghi G, Zanardi F, Appendino G, Rassu G. Chem. Rev. 2000; 100: 1929
- 107 Liu T.-Y, Cui H.-L, Long J, Li B.-J, Wu Y, Ding L.-S, Chen Y.-C. J. Am. Chem. Soc. 2007; 129: 1878
- 108 Niess B, Jørgensen KA. Chem. Commun. 2007; 1620
- 109 Martin SF, Lopez OD. Tetrahedron Lett. 1999; 40: 8949
- 110 Akiyama T, Honma Y, Itoh J, Fuchibe K. Adv. Synth. Catal. 2008; 350: 399
- 111 Giera DS, Sickert M, Schneider C. Org. Lett. 2008; 10: 4259
- 112 Carswell EL, Snapper ML, Hoveyda AH. Angew. Chem. Int. Ed. 2006; 45: 7230 ; Angew. Chem. 2006, 118, 7388
- 113 Wieland LC, Vieira EM, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 570
- 114 Mandai H, Mandai K, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 17961
- 115 González AS, Arrayás RG, Rivero MR, Carretero JC. Org. Lett. 2008; 10: 4335
- 116 Yuan Z.-L, Jiang J.-JShi M. Tetrahedron 2009; 65: 6001
- 117 Deng H.-P, Wei Y, Shi M. Adv. Synth. Catal. 2009; 351: 2897
- 118 Zhao Q.-Y, Yuan Z.-L, Shi M. Tetrahedron: Asymmetry 2010; 21: 943
- 119 Zhao Q.-Y, Yuan Z.-L, Shi M. Adv. Synth. Catal. 2011; 353: 637
- 120 Zhao Q.-Y, Shi M. Tetrahedron 2011; 67: 3724
- 121 Shepherd NE, Tanabe H, Xu Y, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 3666
- 122 Zhou L, Lin L, Ji J, Xie M, Liu X, Feng X. Org. Lett. 2011; 13: 3056