Design and synthesis of spiro bis(1,2,3-triazolium) salts as chiral ionic liquids

Tetrahedron Asymmetry

Volumn 23, Issue 11-12, 2012, Pages 843-851

  Yoshida, Yasushi ^a   Takizawa, Shinobu ^a   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IONIC LIQUID; SPIRO COMPOUND; TRIAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; SYNTHESIS;

EID: 84864261803     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.06.007     Document Type: Article

References (100)

1. Y.L. Angell, and K. Burgess Chem. Soc. Rev. 36 2007 1674
2. S.G. Agalave, S.R. Maujan, and V.S. Pore Chem. Asian J. 6 2011 2696
3. D. Astruc, L. Liang, A. Rapakousiou, and J. Ruiz J. Acc. Chem. Res. 45 2012 630
4. A. Michael J. Prakt. Chem. 48 1893 94
5. R. Huisgen Proc. Chem. Soc. 1961 357
6. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
7. Recent reviews J. Lahann Click Chemistry for Biotechnology and Material Science 2009 Wiley
8. U. Mansfeld, C. Pietsch, R. Hoogenboom, C.R. Becer, and U.S. Schubert Polym. Chem. 1 2010 1560
9. C. Haensch, S. Hoeppener, and U.S. Schubert Chem. Soc. Rev. 39 2010 2323
10. V. Aragao-Leoneti, V.L. Campo, A.S. Gomes, R.A. Field, and I. Carvalho Tetrahedron 66 2010 9475
11. C. Barner-Kowollik, F.E.D. Prez, P. Espeel, C.J. Hawker, T. Junkers, H. Schlaad, and W.V. Camp Angew. Chem., Int. Ed. 50 2011 62
12. Recently, 1,2,3-triazolium salts have been applied in ionic liquids, organocatalysts and N-heterocyclic carbenes chemistries. Ionic liquids S. Hanelt, and J. Liescher Synlett 2008 1058
13. S.S. Khan, S. Hanelt, and J. Liebscher ARKIVOC xii 2009 193
14. Y. Jeong, and J.-S. Ryu J. Org. Chem. 75 2010 4183
15. J.T. Fletcher, M.E. Keeney, and S.E. Walz Synthesis 2010 3339
16. M.-C. Tseng, H.-T. Cheng, M.-J. Shen, and Y.-H. Chu Org. Lett. 13 2011 4434
17. Y. Jeong, D.-Y. Kim, Y. Choi, and J.-S. Ryu Org. Biomol. Chem. 9 2011 374
18. S. Sanghi, E. Willett, C. Versek, M. Tuominen, and E.B. Coughlin RSC Adv. 2 2012 848 Organocatalysts
19. Z. Yacob, J. Shah, J. Leistner, and J. Liebscher Synlett 2008 2342
20. K. Ohmatsu, M. Kiyokawa, and T. Ooi J. Am. Chem. Soc. 133 2011 1307 N-Heterocyclic carbenes
21. P. Mathew, A. Neels, and M. Albrecht J. Am. Chem. Soc. 130 2008 13534
22. T. Karthikeyan, and S. Sankararaman Tetrahedron Lett. 50 2009 5834
23. S.S. Khan, and J. Liebscher Synthesis 2010 2609
24. G. Guisado-Barrios, J. Bouffard, B. Donnadieu, and G. Bertrand Angew. Chem., Int. Ed. 49 2010 4759
25. T. Nakamura, T. Terashima, K. Ogata, and S.-i. Fukuzawa Org. Lett. 13 2011 620
26. Reviews G.B. Bajracharya, M.A. Arai, P.S. Koranne, T. Suzuki, S. Takizawa, and H. Sasai Bull. Chem. Soc. Jpn. 82 2009 285
27. Recent reports T. Tsujihara, K. Takenaka, K. Onitsuka, M. Hatanaka, and H. Sasai J. Am. Chem. Soc. 131 2009 3452
28. K. Takenaka, N. Itoh, and H. Sasai Org. Lett. 11 2009 1483
29. T. Tsujihara, T. Shinohara, K. Takenaka, S. Takizawa, K. Onitsuka, M. Hatanaka, and H. Sasai J. Org. Chem. 74 2009 9274
30. K. Takenaka, T. Nagano, S. Takizawa, and H. Sasai Tetrahedron: Asymmetry 21 2010 379
31. K. Takenaka, Y. Tanigaki, M.L. Patil, C.V.L. Rao, S. Takizawa, T. Suzuki, and H. Sasai Tetrahedron: Asymmetry 21 2010 767
32. K. Takenaka, S.C. Mohanta, M.L. Patil, C.V.L. Rao, S. Takizawa, T. Suzuki, and H. Sasai Org. Lett. 12 2010 3480
33. G.B. Bajracharya, P.S. Koranne, R.N. Nadaf, R.K.M. Gabr, K. Takenaka, S. Takizawa, and H. Sasai Chem. Commun. 46 2010 9064
34. K. Takenaka, M. Akita, Y. Tanigaki, S. Takizawa, and H. Sasai Org. Lett. 13 2011 3506
35. K. Takenaka, S. Hashimoto, S. Takizawa, and H. Sasai Adv. Synth. Catal. 353 2011 1067
36. S. Takizawa, K. Kiriyama, K. Ieki, and H. Sasai Chem. Commun. 47 2011 9227
37. Y. Yoshida, S. Takizawa, and H. Sasai Tetrahedron Lett. 52 2011 6877
38. For recent reviews on chiral ionic liquids, see M.L. Patil, and H. Sasai Chem. Rec. 8 2008 98
39. A. Winkel, P.V.G. Reddy, and R. Wilhelm Synthesis 2008 999
40. X. Chen, X. Li, A. Hu, and F. Wang Tetrahedron: Asymmetry 19 2008 1
41. J.-C. Plaquevent, J. Levillain, F. Guillen, C. Malhiac, and A.-C. Gaumont Chem. Rev. 108 2008 5035
42. K. Bica, and P. Gaertner Eur. J. Org. Chem. 2008 3235
43. P.D. de Maria Angew. Chem., Int. Ed. 47 2008 6960
44. R. Sebesta, I. Kmentova, and S. Toma Green Chem. 10 2008 484
45. M. Gruttadauria, F. Giacalone, and R. Noto Chem. Soc. Rev. 37 2008 1666
46. S. Luo, L. Zhang, and J.-P. Cheng Chem. Asian. J. 4 2009 1184
47. B. Ni, and A.D. Headley Chem. Eur. J. 16 2010 4426
48. B. Ni, Q. Zhang, and A.D. Headley J. Org. Chem. 71 2006 9857 For selected reports on chiral ionic liquids
49. K. Fukumoto, and H. Ohno Chem. Commun. 2006 3081
50. Y. Ishida, D. Sasaki, H. Miyauchi, and K. Saigo Tetrahedron Lett. 47 2006 7973
51. M.L. Patil, C.V.L. Rao, K. Yonezawa, S. Takizawa, K. Onitsuka, and H. Sasai Org. Lett. 8 2006 227
52. M.L. Patil, C.V.L. Rao, S. Takizawa, K. Takenaka, K. Onitsuka, and H. Sasai Tetrahedron 63 2007 12702
53. V. Kumar, C.E. Olsen, S.J.C. Schaffer, V.S. Parmar, and S.V. Malhotra Org. Lett. 9 2007 3905
54. M. Li, S.L. de Rooy, D.K. Bwambok, B. El-Zahab, J.F. DiTusa, and I.M. Warner Chem. Commun. 2009 6922
55. A. Winkel, and R. Wilhelm Eur. J. Org. Chem. 2010 5817
56. In highly enantioselective reactions using ionic liquid supported organocatalysts, see S. Luo, X. Mi, L. Zhang, S. Liu, H. Xu, and J.-P. Cheng Angew. Chem., Int. Ed. 45 2006 3093
57. W. Miao, and T.H. Chan Adv. Synth. Catal. 348 2006 1711
58. L. Zhou, and L. Wang Chem. Lett. 36 2007 628
59. B. Ni, Q. Zhang, and A.D. Headley Green Chem. 9 2007 737
60. S. Luo, L. Zhang, X. Mi, Y. Qiao, and J.-P. Cheng J. Org. Chem. 72 2007 9350
61. S. Hu, T. Jiang, Z. Zhang, A. Zhu, B. Han, V. Song, Y. Xie, and W. Li Tetrahedron Lett. 48 2007 5613
62. L.-Y. Wu, Z.-Y. Yan, Y.-X. Xie, Y.-N. Niua, and Y.-M. Liang Tetrahedron: Asymmetry 18 2007 2086
63. W. Zhou, L.-W. Xu, H.-Y. Qiu, G.-Q. Lai, C.-G. Xia, and J.-X. Jiang Helv. Chim. Acta 91 2008 53
64. D. Chen, M. Schmitkamp, G. Francio, J. Klankermayer, and W. Leitner Angew. Chem., Int. Ed. 47 2008 7339
65. D.E. Siyutkin, A.S. Kucherenko, M.I. Struchkova, and S.G. Zlotin Tetrahedron Lett. 49 2008 1212
66. Y. Qian, S. Xiao, L. Liu, and Y. Wang Tetrahedron: Asymmetry 19 2008 1515
67. B. Ni, Q. Zhang, K. Dhungana, and A.D. Headley Org. Lett. 11 2009 1037
68. L. Zhang, L. Cui, X. Li, J. Li, S. Luo, and J.-P. Cheng Eur. J. Org. Chem. 2010 4876
69. L. Zhang, L. Cui, X. Li, J. Li, S. Luo, and J.-P. Cheng Chem. Eur. J. 16 2010 2045
70. O.V. Maltsev, A.S. Kucherenko, A.L. Chimishkyan, and S.G. Zlotin Tetrahedron: Asymmetry 21 2010 2659
71. D.-Z. Xu, Y. Liu, S. Shi, and Y. Wang Tetrahedron: Asymmetry 21 2010 2530
72. W.-H. Wang, X.-B. Wang, K. Kodama, T. Hirose, and G.-Y. Zhang Tetrahedron 66 2010 4970
73. Y. Qian, X. Zheng, and Y. Wang Eur. J. Org. Chem. 2010 3672
74. X. Zheng, Y.-B. Qian, and Y. Wang Eur. J. Org. Chem. 2010 515
75. O.V. Maltsev, A.O. Chizhov, and S.G. Zlotin Chem. Eur. J. 17 2011 6109
76. N.A. Larionova, A.S. Kucherenko, D.E. Siyutkin, and S.G. Zlotin Tetrahedron 67 2011 1948
77. J. Cybulski, A. Wisniewska, A. Kulig-Adamiak, Z. Dabrowski, T. Praczyk, A. Michalczyk, F. Walkiewicz, K. Materna, and J. Pernak Tetrahedron Lett. 52 2011 1325
78. J. Howarth, K. Hanlon, D. Fayne, and P. McCormac Tetrahedron Lett. 38 1997 3097
79. B. Pegot, G. Vo-Thanh, D. Gori, and A. Loupy Tetrahedron Lett. 45 2004 6425
80. J. Ding, V. Desikan, X. Han, T.L. Xiao, R. Ding, W.S. Jenks, and D.W. Armstrong Org. Lett. 7 2005 335
81. Z. Wang, Q. Wang, Y. Zhang, and W. Bao Tetrahedron Lett. 46 2005 4657
82. T. Biedron, and P.J. Kubisa Polym. Sci. Part A: Polym. Chem. 43 2005 3454
83. W.-H. Ou, and Z.-Z. Huang Green Chem. 8 2006 731
84. R. Gausepohl, P. Buskens, J. Kleinen, A. Bruckmann, C.W. Lehmann, J. Klankermayer, and W. Leitner Angew. Chem., Int. Ed. 45 2006 3689
85. D.K. Mukherjee, and N. Ghosh Catal. Commun. 9 2008 40
86. S. Garre, E. Parker, B.K. Ni, and A.D. Headley Org. Biomol. Chem. 6 2008 3041
87. J. Li, F. Hu, X.-K. Xie, F. Liu, and Z.-Z. Huang Catal. Commun. 11 2009 276
88. O.N.V. Buu, A. Aupoix, N.D.T. Hong, and G. Vo-Thanh New J. Chem. 33 2009 2060
89. G. Fukuhara, C. Chiappe, A. Mele, B. Melai, F. Bellina, and Y. Inoue Chem. Commun. 46 2010 3472
90. T.-K.-T. Truong, and G. Vo-Thanh Tetrahedron 66 2010 5277
91. A.R. Hajipour, and F. Karimi Synth. Commun. 40 2010 1784
92. H.H. Fox, M.O. Wolf, R. O'Dell, B.L. Lin, R.R. Schrock, and M.S. Wrighton J. Am. Chem. Soc. 116 1994 2827
93. I. Ojima, D.F. Kass, and J. Zhu Organometallics 15 1996 5191
94. A.A. Fannin Jr., D.A. Floreani, L.A. King, J.S. Landers, B.J. Piersma, D.J. Stech, R.L. Vaughn, J.S. Wilkes, and J.L. Williams J. Phys. Chem. 88 1984 2614
95. J.D. Holbrey, and K.R. Seddon J. Chem. Soc. Dalton Trans. 1999 2133
96. A.S. Larsen, J.D. Holbrey, F.S. Tham, and C.A. Reed J. Am. Chem. Soc. 122 2000 7264
97. R. Sheldon Chem. Commun. 2001 2399
98. G. Drake, G. Kaplan, L. Hall, T. Hawkins, and J. Larue J. Chem. Cryst. 37 2007 15
99. J.M. Takacs, Z. Xu, X-t Jiang, A.P. Leonov, and G.C. Theriot Org. Lett. 4 2002 3843
100. D.L. Dull, and H.S. Mosher J. Am. Chem. Soc. 89 1967 4230