Recent advances in the trifluoromethylation methodology and new CF3-containing drugs

Journal of Fluorine Chemistry

Volumn 167, Issue , 2014, Pages 37-54

  Zhu, Wei ^a   Wang, Jiang ^a   Wang, Shuni ^a   Gu, Zhanni ^a   Aceña, José Luis ^b   Izawa, Kunisuke ^c   Liu, Hong ^a   Soloshonok, Vadim A ^b,d  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^c Technology Department / Yonezawa Hamari Chemicals Ltd 2 4300 18   (Japan)

^d BASQUE FOUNDATION FOR SCIENCE   (Spain)

Author keywords

Biological activity; Fluorine containing drugs; Methodology; Pharmaceuticals; Trifluoromethylation

Indexed keywords

EID: 85027958002     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2014.06.026     Document Type: Article

References (206)

1. R.E. Banks, B.E. Smart, and J.C. Tatlow Organofluorine Chemistry, Principles and Commercial Applications 1994 Plenum New York
2. H. Hiyama Organofluorine Compounds: Chemistry and Applications 2000 Springer Berlin
3. B. Baasner, H. Hagemann, and J.C. Tatlow Houben-Weyl Methods of Organic Chemistry E10 2000 Thieme Chemistry Stuttgart
4. K.L. Kirk J. Fluor. Chem. 127 2006 1013 1029
5. J.-P. Bégué, and D. Bonnet-Delpon J. Fluor. Chem. 127 2006 992 1012
6. D. O'Hagan J. Fluor. Chem. 131 2010 1071 1081
7. J. Wang, M. Sánchez-Roselló, J.L. Aceña, C. del Pozo, A.E. Sorochinsky, S. Fustero, V.A. Soloshonok, and H. Liu Chem. Rev. 114 2014 2432 2506
8. V.P. Kukhar, A.E. Sorochinsky, and V.A. Soloshonok Future Med. Chem. 1 2009 793 819
9. A.E. Sorochinsky, and V.A. Soloshonok J. Fluor. Chem. 131 2010 127 139
10. J.L. Aceña, A. Simón-Fuentes, and S. Fustero Curr. Org. Chem. 14 2010 928 949
11. K. Mikami, S. Fustero, M. Sánchez-Roselló, J.L. Aceña, V. Soloshonok, and A. Sorochinsky Synthesis 2011 3045 3079
12. J.L. Aceña, A.E. Sorochinsky, and V.A. Soloshonok Synthesis 44 2012 1591 1602
13. K.V. Turcheniuk, V.P. Kukhar, G.-V. Röschenthaler, J.L. Aceña, V.A. Soloshonok, and A.E. Sorochinsky RSC Adv. 3 2013 6693 6716
14. J.L. Aceña, A.E. Sorochinsky, H. Moriwaki, T. Sato, and V.A. Soloshonok J. Fluor. Chem. 155 2013 21 38
15. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
16. G.K.S. Prakash, and A.K. Yudin Chem. Rev. 97 1997 757 786
17. J.-A. Ma, and D. Cahard Chem. Rev. 108 2008 PR1 PR43
18. K.L. Kirk Org. Process Res. Dev. 12 2008 305 321
19. R.J. Lundgren, and M. Stradiotto Angew. Chem. Int. Ed. 49 2010 9322 9324
20. T. Furuya, A.S. Kamlet, and T. Ritter Nature 473 2011 470 477
21. T. Besset, C. Schneider, and D. Cahard Angew. Chem. Int. Ed. 51 2012 5048 5050
22. S. Roy, B.T. Gregg, G.W. Gribble, V.-D. Le, and S. Roy Tetrahedron 67 2011 2161 2195
23. A. Studer Angew. Chem. Int. Ed. 51 2012 8950 8958
24. T. Liu, and Q. Shen Eur. J. Org. Chem. 2012 6679 6687
25. X.-F. Wu, H. Neumann, and M. Beller Chem. Asian J. 7 2012 1744 1754
26. H. Liu, Z. Gu, and X. Jiang Adv. Synth. Catal. 355 2013 617 626
27. X. Liu, and X. Wu Synlett 24 2013 1882 1886
28. J. Xu, X. Liu, and Y. Fu Tetrahedron Lett. 55 2014 585 594
29. E. Merino, C., Nevado, Chem. Soc Rev.,doi:10.1039/C4CS00025 K (in press).
30. F. Swarts Bull. Acad. R. Belg. 24 1892 309
31. H. Urata, and T. Fuchikami Tetrahedron Lett. 32 1991 91 94
32. G.G. Dubinina, H. Furutachi, and D.A. Vicic J. Am. Chem. Soc. 130 2008 8600 8601
33. H. Morimoto, T. Tsubogo, N.D. Litvinas, and J.F. Hartwig Angew. Chem. Int. Ed. 50 2011 3793 3798
34. O.A. Tomashenko, E.C. Escudero-Adán, M. Martínez Belmonte, and V.V. Grushin Angew. Chem. Int. Ed. 50 2011 7655 7659
35. O.A. Tomashenko, and V.V. Grushin Chem. Rev. 111 2011 4475 4521
36. M. Oishi, H. Kondo, and H. Amii Chem. Commun. 2009 1909 1911
37. T. Knauber, F. Arikan, G.-V. Röschenthaler, and L.J. Gooen Chem. Eur. J. 17 2011 2689 2697
38. H. Kondo, M. Oishi, K. Fujikawa, and H. Amii Adv. Synth. Catal. 353 2011 1247 1252
39. A. Zanardi, M.A. Novikov, E. Martin, J. Benet-Buchholz, and V.V. Grushin J. Am. Chem. Soc. 133 2011 20901 20913
40. V.V. Grushin, and W.J. Marshall J. Am. Chem. Soc. 128 2006 12644 12645
41. N.D. Ball, J.W. Kampf, and M.S. Sanford J. Am. Chem. Soc. 132 2010 2878 2879
42. Y. Ye, N.D. Ball, J.W. Kampf, and M.S. Sanford J. Am. Chem. Soc. 132 2010 14682 14687
43. E.J. Cho, T.D. Senecal, T. Kinzel, Y. Zhang, D.A. Watson, and S.L. Buchwald Science 328 2010 1679 1681
44. L. Chu, and F.-L. Qing Org. Lett. 12 2010 5060 5063
45. T.D. Senecal, A.T. Parsons, and S.L. Buchwald J. Org. Chem. 76 2011 1174 1176
46. B.A. Khan, A.E. Buba, and L.J. Gooen Chem. Eur. J. 18 2012 1577 1581
47. C.-P. Zhang, J. Cai, C.-B. Zhou, X.-P. Wang, X. Zheng, Y.-C. Gu, and J.-C. Xiao Chem. Commun. 47 2011 9516 9518
48. Y. Ye, S.A. Künzi, and M.S. Sanford Org. Lett. 14 2012 4979 4981
49. P. Novák, A. Lishchynskyi, and V.V. Grushin Angew. Chem. Int. Ed. 51 2012 7767 7770
50. X. Jiang, L. Chu, and F.-L. Qing J. Org. Chem. 77 2012 1251 1257
51. T. Liu, and Q. Shen Org. Lett. 13 2011 2342 2345
52. J. Xu, D.-F. Luo, B. Xiao, Z.-J. Liu, T.-J. Gong, Y. Fu, and L. Liu Chem. Commun. 47 2011 4300 4302
53. Y. Ye, and M.S. Sanford J. Am. Chem. Soc. 134 2012 9034 9037
54. Y. Li, L. Wu, H. Neumann, and M. Beller Chem. Commun. 49 2013 2628 2630
55. J.-J. Dai, C. Fang, B. Xiao, J. Yi, J. Xu, Z.-J. Liu, X. Lu, L. Liu, and Y. Fu J. Am. Chem. Soc. 135 2013 8436 8439
56. X. Wang, Y. Xu, F. Mo, G. Ji, D. Qiu, J. Feng, Y. Ye, S. Zhang, Y. Zhang, and J. Wang J. Am. Chem. Soc. 135 2013 10330 10333
57. Y. Ye, S.H. Lee, and M.S. Sanford Org. Lett. 13 2011 5464 5467
58. D.A. Nagib, and D.W.C. MacMillan Nature 480 2011 224 228
59. X. Wang, L. Truesdale, and J.-Q. Yu J. Am. Chem. Soc. 132 2010 3648 3649
60. X.-G. Zhang, H.-X. Dai, M. Wasa, and J.-Q. Yu J. Am. Chem. Soc. 134 2012 11948 11951
61. L.-S. Zhang, K. Chen, G. Chen, B.-J. Li, S. Luo, Q.-Y. Guo, J.-B. Wei, and Z.-J. Shi Org. Lett. 15 2013 10 13
62. A. Hafner, and S. Bräse Angew. Chem. Int. Ed. 51 2012 3713 3715
63. N.D. Litvinas, P.S. Fier, and J.F. Hartwig Angew. Chem. Int. Ed. 51 2012 536 539
64. T. Liu, X. Shao, Y. Wu, and Q. Shen Angew. Chem. Int. Ed. 51 2012 540 543
65. Y. Zeng, L. Zhang, Y. Zhao, C. Ni, J. Zhao, and J. Hu J. Am. Chem. Soc. 135 2013 2955 2958
66. K.-P. Wang, S.Y. Yun, P. Mamidipalli, and D. Lee Chem. Sci. 4 2013 3205 3211
67. F. Cottet, and M. Schlosser Eur. J. Org. Chem. 2002 327 330
68. C.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, and J.-C. Xiao Angew. Chem. Int. Ed. 50 2011 1896 1900
69. X. Mu, S. Chen, X. Zhen, and G. Liu Chem. Eur. J. 17 2011 6039 6042
70. L. Chu, and F.-L. Qing J. Am. Chem. Soc. 134 2012 1298 1304
71. N. Iqbal, S. Choi, E. Ko, and E.J. Cho Tetrahedron Lett. 53 2012 2005 2008
72. Y. Ji, T. Brueckl, R.D. Baxter, Y. Fujiwara, I.B. Seiple, S. Su, D.G. Blackmond, and P.S. Baran Proc. Natl. Acad. Sci. U.S.A 108 2011 14411 14415
73. L. Chu, and F.-L. Qing J. Am. Chem. Soc. 132 2010 7262 7263
74. A.T. Parsons, T.D. Senecal, and S.L. Buchwald Angew. Chem. Int. Ed. 51 2012 2947 2950
75. Y. Yasu, T. Koike, and M. Akita Chem. Commun. 49 2013 2037 2039
76. E.J. Cho, and S.L. Buchwald Org. Lett. 13 2011 6552 6555
77. Z. He, T. Luo, M. Hu, Y. Cao, and J. Hu Angew. Chem. Int. Ed. 51 2012 3944 3947
78. Z. Li, Z. Cui, and Z.-Q. Liu Org. Lett. 15 2013 406 409
79. C. Feng, and T.-P. Loh Chem. Sci. 3 2012 3458 3462
80. H. Jiang, C. Huang, J. Guo, C. Zeng, Y. Zhang, and S. Yu Chem. Eur. J. 18 2012 15158 15166
81. N. Iqbal, S. Choi, E. Kim, and E.J. Cho J. Org. Chem. 77 2012 11383 11387
82. P.G. Janson, I. Ghoneim, N.O. Ilchenko, and K.J. Szabó Org. Lett. 14 2012 2882 2885
83. H. Egami, R. Shimizu, and M. Sodeoka Tetrahedron Lett. 53 2012 5503 5506
84. N. Shibata, S. Mizuta, and H. Kawai Tetrahedron: Asymmetry 19 2008 2633 2644
85. T. Umemoto, and S. Ishihara Tetrahedron Lett. 31 1990 3579 3582
86. I. Kieltsch, P. Eisenberger, and A. Togni Angew. Chem. Int. Ed. 46 2007 754 757
87. D.A. Nagib, M.E. Scott, and D.W.C. MacMillan J. Am. Chem. Soc. 131 2009 10875 10877
88. P.V. Pham, D.A. Nagib, and D.W.C. MacMillan Angew. Chem. Int. Ed. 50 2011 6119 6122
89. A.E. Allen, and D.W.C. MacMillan J. Am. Chem. Soc. 132 2010 4986 4987
90. Q.-H. Deng, H. Wadepohl, and L.H. Gade J. Am. Chem. Soc. 134 2012 10769 10772
91. T. Umemoto, and K. Adachi J. Org. Chem. 59 1994 5692 5699
92. V. Matoušek, A. Togni, V. Bizet, and D. Cahard Org. Lett. 13 2011 5762 5765
93. A.T. Herrmann, L.L. Smith, and A. Zakarian J. Am. Chem. Soc. 134 2012 6976 6979
94. P. Novák, A. Lishchynskyi, and V.V. Grushin J. Am. Chem. Soc. 134 2012 16167 16170
95. M. Hu, C. Ni, and J. Hu J. Am. Chem. Soc. 134 2012 15257 15260
96. H. Kawai, T. Furukawa, Y. Nomura, E. Tokunaga, and N. Shibata Org. Lett. 13 2011 3596 3599
97. Y. Miyake, S. Ota, and Y. Nishibayashi Chem. Eur. J. 18 2012 13255 13258
98. R. Shimizu, H. Egami, Y. Hamashima, and M. Sodeoka Angew. Chem. Int. Ed. 51 2012 4577 4580
99. S. Mizuta, O. Galicia-López, K.M. Engle, S. Verhoog, K. Wheelhouse, G. Rassias, and V. Gouverneur Chem. Eur. J. 18 2012 8583 8587
100. S. Mizuta, K.M. Engle, S. Verhoog, O. Galicia-López, M. O'Duill, M. Médebielle, K. Wheelhouse, G. Rassias, A.L. Thompson, and V. Gouverneur Org. Lett. 15 2013 1250 1253
101. A.T. Parsons, and S.L. Buchwald Angew. Chem. Int. Ed. 50 2011 9120 9123
102. X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, and J. Wang J. Am. Chem. Soc. 133 2011 16410 16413
103. J. Xu, Y. Fu, D.-F. Luo, Y.-Y. Jiang, B. Xiao, Z.-J. Liu, T.-J. Gong, and L. Liu J. Am. Chem. Soc. 133 2011 15300 15303
104. D.-F. Lu, C.-L. Zhu, and H. Xu Chem. Sci. 4 2013 2478 2482
105. Y. Yasu, T. Koike, and M. Akita Angew. Chem. Int. Ed. 51 2012 9567 9571
106. R. Zhu, and S.L. Buchwald J. Am. Chem. Soc. 134 2012 12462 12465
107. X. Liu, F. Xiong, X. Huang, L. Xu, P. Li, and X. Wu Angew. Chem. Int. Ed. 52 2013 6962 6966
108. Y. Li, and A. Studer Angew. Chem. Int. Ed. 51 2012 8221 8224
109. Y. Yasu, T. Koike, and M. Akita Org. Lett. 15 2013 2136 2139
110. X. Mu, T. Wu, H.-y. Wang, Y.-l. Guo, and G. Liu J. Am. Chem. Soc. 134 2012 878 881
111. H. Egami, R. Shimizu, S. Kawamura, and M. Sodeoka Angew. Chem. Int. Ed. 52 2013 4000 4003
112. X. Wu, L. Chu, and F.-L. Qing Angew. Chem. Int. Ed. 52 2013 2198 2202
113. S. Mizuta, S. Verhoog, K.M. Engle, T. Khotavivattana, M. O'Duill, K. Wheelhouse, G. Rassias, M. Médebielle, and V. Gouverneur J. Am. Chem. Soc. 135 2013 2505 2508
114. D.J. Wilger, N.J. Gesmundo, and D.A. Nicewicz Chem. Sci. 4 2013 3160 3165
115. J. Xu, B. Xiao, C.-Q. Xie, D.-F. Luo, L. Liu, and Y. Fu Angew. Chem. Int. Ed. 51 2012 12551 12554
116. Y. Li, F. Liang, Q. Li, Y.-C. Xu, Q.-R. Wang, and L. Jiang Org. Lett. 13 2011 6082 6085
117. Y. Pan, S. Wang, C.W. Kee, E. Dubuisson, Y. Yang, K.P. Loh, and C.-H. Tan Green Chem. 13 2011 3341 3344
118. T. Umemoto, K. Adachi, and S. Ishihara J. Org. Chem. 72 2007 6905 6917
119. K. Niedermann, N. Früh, R. Senn, B. Czarniecki, R. Verel, and A. Togni Angew. Chem. Int. Ed. 51 2012 6511 6515
120. F.R. Leroux, B. Manteau, J.-P. Vors, and S. Pazenok Beilstein J. Org. Chem. 4 2008 10.3762/bjoc.4.13
121. R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, and A. Togni Angew. Chem. Int. Ed. 48 2009 4332 4336
122. K. Stanek, R. Koller, and A. Togni J. Org. Chem. 73 2008 7678 7685
123. S. Fantasia, J.M. Welch, and A. Togni J. Org. Chem. 75 2010 1779 1782
124. A. Tlili, and T. Billard Angew. Chem. Int. Ed. 52 2013 6818 6819
125. F. Toulgoat, S. Alazet, and T. Billard Eur. J. Org. Chem. 2014 2415 2428
126. S. Capone, I. Kieltsch, O. Flogel, G. Lelais, A. Togni, and D. Seebach Helv. Chim. Acta 91 2008 2035 2056
127. R. Koller, Q. Huchet, P. Battaglia, J.M. Welch, and A. Togni Chem. Commun. 2009 5993 5995
128. H. Ohkura, D.O. Berbasov, and V.A. Soloshonok Tetrahedron 59 2003 1647 1656
129. T. Fuchikami, and I. Ojima Tetrahedron Lett. 23 1982 4099 4100
130. I. Ojima, K. Kato, M. Okabe, and T. Fuchikami J. Am. Chem. Soc. 109 1987 7714 7720
131. I. Ojima, M. Okabe, K. Kato, H.B. Kwon, and I.T. Horváth J. Am. Chem. Soc. 110 1988 150 157
132. I. Ojima, K. Kato, K. Nakahashi, T. Fuchikami, and M. Fujita J. Org. Chem. 54 1989 4511 4522
133. V.A. Soloshonok, D.V. Avilov, and V.P. Kukhar Tetrahedron 52 1996 12433 12442
134. V.A. Soloshonok, and T. Hayashi Tetrahedron: Asymmetry 5 1994 1091 1094
135. T. Katagiri, S. Yamaji, M. Handa, M. Irie, and K. Uneyama Chem. Commun. 2001 2054 2055
136. T. Fuchikami, and I. Ojima J. Am. Chem. Soc. 104 1982 3527 3529
137. T. Fuchikami, K. Ohishi, and I. Ojima J. Org. Chem. 48 1983 3803 3807
138. I. Ojima, and H.B. Kwon J. Am. Chem. Soc. 110 1988 5617 5621
139. V.A. Soloshonok, and T. Hayashi Tetrahedron Lett. 35 1994 2713 2716
140. V.A. Soloshonok, T. Hayashi, K. Ishikawa, and N. Nagashima Tetrahedron Lett. 35 1994 1055 1058
141. S.D. Young, S.F. Britcher, L.O. Tran, L.S. Payne, W.C. Lumma, T.A. Lyle, J.R. Huff, P.S. Anderson, D.B. Olsen, S.S. Carroll, D.J. Pettibone, J.A. O'Brien, R.G. Ball, S.K. Balani, J.H. Lin, I.-W. Chen, W.A. Schleif, V.V. Sardana, W.J. Long, V.W. Byrnes, and E.A. Emini Antimicrob. Agents Chemother. 39 1995 2602 2605
142. J. Balzarini Curr. Top. Med. Chem. 4 2004 921 944
143. D. Kim, L. Wang, M. Beconi, G.J. Eiermann, M.H. Fisher, H. He, G.J. Hickey, J.E. Kowalchick, B. Leiting, K. Lyons, F. Marsilio, M.E. McCann, R.A. Patel, A. Petrov, G. Scapin, S.B. Patel, R.S. Roy, J.K. Wu, M.J. Wyvratt, B.B. Zhang, L. Zhu, N.A. Thornberry, and A.E. Weber J. Med. Chem. 48 2005 141 151
144. N.A. Thornberry, and A.E. Weber Curr. Top. Med. Chem. 7 2007 557 568
145. T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, and P.C. Isakson J. Med. Chem. 40 1997 1347 1365
146. A.K. Chakraborti, S.K. Garg, R. Kumar, H.F. Motiwala, and P.S. Jadhavar Curr. Med. Chem. 17 2010 1563 1593
147. H. Nagaya, N. Inatomi, A. Nohara, and H. Satoh Biochem. Pharmacol. 42 1991 1875 1878
148. N. Franceschini, M.S. Joy, and A. Kshirsagar Expert Opin. Invest. Drugs 12 2003 1413 2142
149. C. Marcocci, and F. Cetani J. Endocrinol. Invest. 35 2012 90 95
150. S.V. Frye, C.D. Haffner, P.R. Maloney, R.N. Hiner, G.F. Dorsey, R.A. Noe, R.J. Unwalla, K.W. Batchelor, H.N. Bramson, J.D. Stuart, S.L. Schweiker, J. Van Arnold, D.M. Bickett, M.L. Moss, G. Tian, F.W. Lee, T.K. Tippin, M.K. James, M.K. Grizzle, J.E. Long, and D.K. Croom J. Med. Chem. 38 1995 2621 2627
151. S.V. Frye Curr. Top. Med. Chem. 6 2006 405 421
152. P.A. Netland, T. Landry, E.K. Sullivan, R. Andrew, L. Silver, A. Weiner, S. Mallick, J. Dickerson, M.V.W. Bergamini, S.M. Robertson, and A.A. Davis Am. J. Ophthalmol. 132 2001 472 484
153. B.J. Deadman, M.D. Hopkin, I.R. Baxendale, and S.V. Ley Org. Biomol. Chem. 11 2013 1700 1766
154. M. Crockett, and K.C. Kain Expert Opin. Inv. Drugs 16 2007 705 715
155. N.P.D. Nanayakkara, A.L. Ager, M.S. Bartlett, V. Yardley, S.L. Croft, I.A. Khan, J.D. McChesney, and L.A. Walker Antimicrob. Agents Chemother. 52 2008 2130 2137
156. H. Shiraki, M.P. Kozar, V. Melendez, T.H. Hudson, C. Ohrt, A.J. Magill, and A.J. Lin J. Med. Chem. 54 2011 131 142
157. C.O. Ugwuegbulam, J.E. Foy, PCT Int. Appl., WO9713753A1.
158. D. Bell, B.J. Davies, P.M. Kincey, PCT Int. Appl., WO2003093239A2.
159. U. Lucking, R. Jautelat, M. Kruger, T. Brumby, P. Lienau, M. Schafer, H. Briem, J. Schulze, A. Hillisch, A. Reichel, A.M. Wengner, and G. Siemeister ChemMedChem 8 2013 1067 1085
160. G. Siemeister, U. Lucking, A.M. Wengner, P. Lienau, W. Steinke, C. Schatz, D. Mumberg, and K. Ziegelbauer Mol. Cancer Ther. 11 2012 2265 2273
161. U. Lucking Angew. Chem. Int. Ed. 52 2013 9399 9408
162. J. Krüger, J. Gries, K. Lovis, J. Hassfeld, U.S. Patent, US2013245261A1.
163. J. Kath, M. Luzzio, U.S. Patent, US20050256125A1.
164. D. Uraguchi, K. Yamamoto, Y. Ohtsuka, K. Tokuhisa, and T. Yamakawa Appl. Catal. A 342 2008 137 143
165. S.J. Park, H. Baars, S. Mersmann, H. Buschmann, J.M. Baron, P.M. Amman, K. Czaja, H. Hollert, K. Bluhm, R. Redelstein, and C. Bolm ChemMedChem 8 2013 217 220
166. Y. Cheng, W. Dong, L. Wang, K. Parthasarathy, and C. Bolm Org. Lett. 16 2014 2000 2002
167. V. Bizet, R. Kowalczyk, and C. Bolm Chem. Soc. Rev. 43 2014 2426 2438
168. V. Bizet, L. Buglioni, and C. Bolm Angew. Chem. Int. Ed. 53 2014 5639 5642
169. V.A. Soloshonok, and D.O. Berbasov Chim. Oggi - Chem. Today 24 2006 44 47
170. H. Ueki, M. Yasumoto, and V.A. Soloshonok Tetrahedron: Asymmetry 21 2010 1396 1400
171. V.A. Soloshonok, C. Roussel, O. Kitagawa, and A.E. Sorochinsky Chem. Soc. Rev. 41 2012 4180 4188
172. P. Diter, S. Taudien, O. Samuel, and H.B. Kagan J. Org. Chem. 59 1994 370 373
173. W. Song, Y. Zhou, Y. Fu, and W. Xu Tetrahedron: Asymmetry 24 2013 909 912
174. A. Wzorek, K.D. Klika, J. Drabowicz, A. Sato, J.L. Aceña, and V.A. Soloshonok Org. Biomol. Chem. 12 2014 4738 4746
175. F. Mauler, J. Mittendorf, E. Horváth, and J. de Vry J. Pharmacol. Exp. Ther. 302 2002 359 368
176. F. Mauler, V. Hinz, K.-H. Augstein, M. Fabender, and E. Horváth Brain Res. 989 2003 99 111
177. F. Mauler, E. Horváth, J. De Vry, R. Jäger, T. Schwarz, S. Sandmann, C. Weinz, R. Heinig, and M. Böttcher CNS Drug Rev. 9 2003 343 358
178. J. De Vry, and K.R. Jentzsch Eur. J. Pharmacol. 457 2002 147 152
179. J. Wang, D. Lin, S. Zhou, X. Ding, V.A. Soloshonok, and H. Liu J. Org. Chem. 76 2011 684 687
180. J. De Vry, D. Denzer, E. Reissmueller, M. Eijckenboom, M. Heil, H. Meier, and F. Mauler J. Pharmacol. Exp. Ther. 310 2004 620 632
181. J. Mittendorf, J. Dressel, M. Matzke, J. Keldenich, K.H. Mohrs, S. Raddatz, J. Franz, P. Spreyer, V. Vöhringer, J. Schumacher, U.S. Patent 6262112, 2001.
182. J. Mittendorf, J. Dressel, M. Matzke, J. Keldenich, F. Mauler, J. M. V. De Vry, J. Franz, P. Spreyer, V. Vöhringer, J. Schumacher, U.S. Patent 6545050, 2003.
183. V.A. Soloshonok Angew. Chem. Int. Ed. 45 2006 766 769
184. V.A. Soloshonok, H. Ueki, M. Yasumoto, S. Mekala, J.S. Hirschi, and D.A. Singleton J. Am. Chem. Soc. 129 2007 12112 12113
185. A.E. Sorochinsky, J.L. Aceña, and V.A. Soloshonok Synthesis 45 2013 141 152
186. H. Doucet, E. Fernandez, T.P. Layzell, and J.M. Brown Chem. Eur. J. 5 1999 1320 1330
187. A.E. Sorochinsky, T. Katagiri, T. Ono, A. Wzorek, J.L. Aceña, and V.A. Soloshonok Chirality 25 2013 365 368
188. M. Albrecht, V.A. Soloshonok, L. Schrader, M. Yasumoto, and M.A. Suhm J. Fluor. Chem. 131 2010 495 504
189. S. Ogawa, T. Nishimine, E. Tokunaga, S. Nakamura, and N. Shibata J. Fluor. Chem. 131 2010 521 524
190. S. Pan, X. Wu, J. Jiang, W. Gao, Y. Wan, D. Cheng, D. Han, J. Liu, N.P. Englund, Y. Wang, S. Peukert, K. Miller-Moslin, J. Yuan, R. Guo, M. Matsumoto, A. Vattay, Y. Jiang, J. Tsao, F. Sun, A.C. Pferdekamper, S. Dodd, T. Tuntland, W. Maniara, J.F. Kelleher, Y.-m. Yao, M. Warmuth, J. Williams, and M. Dorsch ACS Med. Chem. Lett. 1 2010 130 134
191. D.A. Irvine, and M. Copland Blood 119 2012 2196 2204
192. A.A. Merchant, and W. Matsui Clin. Cancer Res. 16 2010 3130 3140
193. B. Hu, J. Cai, J. Chen, M. Cao, P. Wang, X. Zong, R. Zhang, and M. Ji J. Chem. Res. 38 2014 18 20
194. A.E. Bailey, D.R. Hill, C.-N.W. Hsiao, R. Kurukulasuriya, S. Wittenberger, T. McDermott, M.A. McLaughlin, U.S. Patent 0019539, 2002.
195. K.R. Benson, J. Hickey, W.S. DerWin, M.J. Fifolt, S. Mandal, U.S. Patent 6118028, 2000.
196. H. Hayashi, H. Sonoda, K.I. Goto, K. Fukumura, J. Naruse, H. Oikawa, T. Nagata, T. Shimaoka, T. Yasutake, H. Umetani, T. Kitashima, U.S. Patent 6417361, 2002.
197. C. Tse, A.R. Shoemaker, J. Adickes, M.G. Anderson, J. Chen, S. Jin, E.F. Johnson, K.C. Marsh, M.J. Mitten, P. Nimmer, L. Roberts, S.K. Tahir, Y. Mao, X.F. Yang, H.C. Zhang, S. Fesik, S.H. Rosenberg, and S.W. Elmore Cancer Res. 68 2008 3421 3428
198. A.M. Petros, J. Dinges, D.J. Augeri, S.A. Baumeister, D.A. Betebenner, M.G. Bures, S.W. Elmore, P.J. Hajduk, M.K. Joseph, S.K. Landis, D.G. Nettesheim, S.H. Rosenberg, W. Shen, S. Thomas, X.L. Wang, I. Zanze, H.C. Zhang, and S.W. Fesik J. Med. Chem. 49 2006 656 663
199. M.D. Wendt, W. Shen, A. Kunzer, W.J. McClellan, M. Bruncko, T.K. Oost, H. Ding, M.K. Joseph, H. Zhang, P.M. Nimmer, S.C. Ng, A.R. Shoemaker, A.M. Petros, A. Oleksijew, K. Marsh, J. Bauch, T. Oltersdorf, B.A. Belli, D. Martineau, S.W. Fesik, S.H. Rosenberg, and S.W. Elmore J. Med. Chem. 49 2006 1165 1181
200. M. Bruncko, T.K. Oost, B.A. Belli, H. Ding, M.K. Joseph, A. Kunzer, D. Martineau, W.J. McClellan, M. Mitten, S.C. Ng, P.M. Nimmer, T. Oltersdorf, C.M. Park, A.M. Petros, A.R. Shoemaker, X. Song, X. Wang, M.D. Wendt, H. Zhang, S.W. Fesik, S.H. Rosenberg, and S.W. Elmore J. Med. Chem. 50 2007 641 662
201. C.M. Park, M. Bruncko, J. Adickes, J. Bauch, H. Ding, A. Kunzer, K.C. Marsh, P. Nimmer, A.R. Shoemaker, X. Song, S.K. Tahir, C. Tse, X. Wang, M.D. Wendt, X. Yang, H. Zhang, S.W. Fesik, S.H. Rosenberg, and S.W. Elmore J. Med. Chem. 51 2008 6902 6915
202. X.X. Lin, G.M. Wang, H.F. Li, Y.Y. Huang, W.M. He, D.D. Ye, K.W. Huang, Y.F. Yuan, and Z.Q. Weng Tetrahedron 69 2013 2628 2632
203. R.P. Singh, G.F. Cao, R.L. Kirchmeier, and J.M. Shreeve J. Org. Chem. 64 1999 2873 2876
204. Y. Chang, and C. Cai J. Fluor. Chem. 126 2005 937 940
205. V.I. Popov, V.N. Boiko, and L.M. Yagupolskii J. Fluor. Chem. 21 1982 365 369
206. V.A. Soloshonok, V.P. Kukhar, Y. Pustovit, and V.A. Nazaretyan Synlett 1992 657 658