Large-scale Mannich-type reactions of (SS)-N-tert- butanesulfinyl-(3,3,3)-trifluoroacetaldimine with C-nucleophiles

Journal of Fluorine Chemistry

Volumn 165, Issue , 2014, Pages 67-75

  Xie, Chen ^a   Mei, Haibo ^a   Wu, Lingmin ^a   Han, Jianlin ^a,b   Soloshonok, Vadim A ^c,d   Pan, Yi ^a  

^a NANJING UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

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

^d BASQUE FOUNDATION FOR SCIENCE   (Spain)

Author keywords

Biologically active compounds; Large scale; Mannich reaction; Trifluoromethyl amino compounds

Indexed keywords

EID: 84904179780     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2014.06.015     Document Type: Article

References (102)

1. 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
2. H.J. Bohm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Muller, U. Obst-Sander, and M. Stahl ChemBioChem 5 2004 637
3. C. Isanbor, and D. O'Hagan J. Fluor. Chem. 127 2006 303
4. J.P. Begue, and D. Bonnet-Delpon J. Fluor. Chem. 127 2006 992
5. K.L. Kirk J. Fluor. Chem. 127 2006 1013
6. W.K. Hagmann J. Med. Chem. 51 2008 4359
7. D. O'Hagan J. Fluor. Chem. 131 2010 1071
8. X. Ji, M.B. Su, J. Wang, G.H. Deng, S.S. Deng, Z. Li, C.L. Tang, J.Y. Li, J. Li, L.X. Zhao, H.L. Jiang, and H. Liu Eur. J. Med. Chem. 75 2014 111
9. J. Wang, Y. Feng, X. Ji, G.H. Deng, Y. Leng, and H. Liu Bioorg. Med. Chem. 21 2013 7418
10. X. Zhang, T. Peng, X. Ji, J. Li, L.J. Tong, Z. Li, W. Yang, Y.G. Xu, M.Y. Li, J. Ding, H.L. Jiang, H. Xie, and H. Liu Bioorg. Med. Chem. 21 2013 7988
11. X. Ji, T. Peng, X. Zhang, J. Li, W. Yang, L.J. Tong, R. Qu, H.L. Jiang, J. Ding, H. Xie, and H. Liu Bioorg. Med. Chem. 22 2014 2366
12. T. Furuya, A.S. Kamlet, and T. Ritter Nature 473 2011 470
13. O.A. Tomashenko, and V.V. Grushin Chem. Rev. 111 2011 4475
14. S. Roy, B.T. Gregg, G.W. Gribble, V.D. Le, and S. Roy Tetrahedron 67 2011 2161
15. A. Studer Angew. Chem. Int. Ed. 51 2012 8950
16. T. Besset, C. Schneider, and D. Cahard Angew. Chem. Int. Ed. 51 2012 5048
17. Y. Ye, and M.S. Sanford Synlett 23 2012 2005
18. T. Liu, and Q. Shen Eur. J. Org. Chem. 2012 6679
19. H. Liu, Z. Gu, and X. Jiang Adv. Synth. Catal. 355 2013 617
20. I. Ojima, J.R. McCarthy, and J.T. Welch Biomedical Frontiers of Fluorine Chemistry 1996 American Chemical Society Washington DC 639 Proceedings of the ACS Symposium Series
21. R. Filler, Y. Kobayashi, and Y.L. Yagulpolskii Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications 1993 Elsevier Amsterdam
22. J.P. Bégué, and D. Bonnet-Delpon Bioorganic and Medicinal Chemistry of Fluorine 2008 John Wiley & Sons, Inc. Hoboken, USA
23. J.L. Aceña, A. Simón-Fuentes, and S. Fustero Curr. Org. Chem. 14 2010 928
24. J. Han, A.E. Sorochinsky, T. Ono, and V.A. Soloshonok Curr. Org. Synth. 8 2011 281
25. K.V. Turcheniuk, V.P. Kukhar, G.V. Roeschenthaler, J.L. Acena, V.A. Soloshonok, and A.E. Sorochinsky RSC Adv. 3 2013 6693
26. J.L. Aceña, A.E. Sorochinsky, and V.A. Soloshonok Synthesis 2012 1591
27. K. Mikami, S. Fustero, M. Sánchez-Roselló, J.L. Aceña, V.A. Soloshonok, and A.E. Sorochinsky Synthesis 2011 3045
28. A.E. Sorochinsky, and V.A. Soloshonok J. Fluor. Chem. 131 2010 127
29. V.P. Kukhar, A.E. Sorochinsky, and V.A. Soloshonok Futur. Med. Chem. 1 2009 793
30. J.Y. Gauthier, N. Chauret, W. Cromlish, S. Desmarais, T. Duong le, J.P. Falgueyret, D.B. Kimmel, S. Lamontagne, S. Leger, T. LeRiche, C.S. Li, F. Masse, D.J. McKay, D.A. Nicoll-Griffith, R.M. Oballa, J.T. Palmer, M.D. Percival, D. Riendeau, J. Robichaud, G.A. Rodan, S.B. Rodan, C. Seto, M. Therien, V.L. Truong, M.C. Venuti, G. Wesolowski, R.N. Young, R. Zamboni, and W.C. Black Bioorg. Med. Chem. Lett. 18 2008 923
31. F. Gosselin, P.D. O'Shea, S. Roy, R.A. Reamer, C.Y. Chen, and R.P. Volante Org. Lett. 7 2005 355
32. G. Hughes, P.N. Devine, J.R. Naber, P.D. O'Shea, B.S. Foster, D.J. McKay, and R.P. Volante Angew. Chem. Int. Ed. 46 2007 1839
33. Y.Q. Zhang, J.D. Liu, and H. Xu Org. Biomol. Chem. 11 2013 6242
34. S. Okusu, H. Kawai, X.H. Xu, E. Tokunaga, and N. Shibata J. Fluor. Chem. 143 2012 216
35. L. Bernardi, E. Indrigo, S. Pollicino, and A. Ricci Chem. Commun. 48 2012 1428
36. A.D. Dilman, and V.V. Levin Eur. J. Org. Chem. 2011 831
37. W. Xu, and W.R. Dolbier Jr. J. Org. Chem. 70 2005 4741
38. T. Ono, V.P. Kukhar, and V.A. Soloshonok J. Org. Chem. 61 1996 6563
39. O.O. Fadeyi, and C.W. Lindsley Org. Lett. 11 2009 943
40. G. Dutheuil, L. Bailly, S. Couve-Bonnaire, and X. Pannecoucke J. Fluor. Chem. 128 2007 34
41. J.P. Bégué, D. Bonnet-Delpon, B. Crousse, and Legros J. Chem. Soc. Rev. 34 2005 562
42. G.F. de Trocóniz, A.M.O. de Retana, S. Pascual, J.M. Ezpeleta, and Palacios F. Eur. J. Org. Chem. 2013 5614
43. V.A. Soloshonok, and T. Ono Tetrahedron 52 1996 14701
44. V.A. Soloshonok, A.G. Kirilenko, V.P. Kukhar, and G. Resnati Tetrahedron Lett. 35 1994 3119
45. V.A. Soloshonok, H. Ohkura, and M. Yasumoto J. Fluor. Chem. 127 2006 930
46. V.A. Soloshonok, and M. Yasumoto J. Fluor. Chem. 128 2007 170
47. H. Pan, Y. Xie, M. Liu, and Y. Shi RSC Adv. 4 2014 2389
48. A. Hjelmencrantz, and U. Berg J. Org. Chem. 67 2002 3585
49. S. Bachmann, K.R. Knudsen, and K.A. Jørgensen Org. Biomol. Chem. 2 2004 2044
50. X. Xiao, Y. Xie, C. Su, M. Liu, and Y. Shi J. Am. Chem. Soc. 133 2011 12914
51. X. Xiao, M. Liu, C. Rong, F. Xue, S. Li, Y. Xie, and Y. Shi Org. Lett. 14 2012 5270
52. V.L. Truong, M.S. Ménard, and I. Dion Org. Lett. 9 2007 683
53. V.L. Truong, and J.Y. Pfeiffer Tetrahedron Lett. 50 2009 1633
54. H. Mimura, K. Kawada, T. Yamashita, T. Sakamoto, and Y. Kikugawa J. Fluor. Chem. 131 2010 477
55. N. Shibata, T. Nishimine, N. Shibata, E. Tokunaga, K. Kawada, T. Kagawa, A.E. Sorochinsky, and V.A. Soloshonok Chem. Commun. 48 2012 4124
56. K.V. Turcheniuk, K.O. Poliashko, V.P. Kukhar, A.B. Rozhenko, V.A. Soloshonok, and A.E. Sorochinsky Chem. Commun. 48 2012 11519
57. Y. Liu, J. Liu, Y. Huang, and F.L. Qing Chem. Commun. 49 2013 7492
58. N. Plobeck, and D. Powell Tetrahedron: Asymmetry 13 2002 303
59. H. Zhang, Y. Li, W. Xu, W. Zheng, P. Zhou, and Z. Sun Org. Biomol. Chem. 9 2011 6502
60. G.V. Röschenthaler, V.P. Kukhar, I.B. Kulik, M.Y. Belik, A.E. Sorochinsky, E.B. Rusanov, and V.A. Soloshonok Tetrahedron Lett. 53 2012 539
61. M.V. Shevchuk, V.P. Kukhar, G.V. Roeschenthaler, B.S. Bassil, K. Kawada, V.A. Soloshonok, and A.E. Sorochinsky RSC Adv. 3 2013 6479
62. M. Liu, and M.P. Sibi Tetrahedron 58 2002 7991
63. D. Seebach, T. Kimmerlin, R. Sebesta, M.A. Campo, and A.K. Beck Tetrahedron 60 2004 7455
64. V.A. Soloshonok, V.K. Svedas, V.P. Kukhar, A.G. Kirilenko, A.V. Rybakova, V.A. Solodenko, N.A. Fokina, O.V. Kogut, I.Y. Galaev, E.V. Kozlova, I.P. Shishkina, and S.V. Galushko Synlett 1993 339
65. N.N. Sergeeva, A.S. Golubev, L. Hennig, M. Findeisen, E. Paetzold, G. Oehme, and K. Burger J. Fluor. Chem. 111 2000 41
66. J. Takaya, H. Kagoshim, and T. Akiyama Org. Lett. 2 2000 1577
67. V.A. Soloshonok, H. Ohkura, A. Sorochinsky, N. Voloshin, A. Markovsky, M. Belik, and T. Yamazaki Tetrahedron Lett. 43 2002 5445
68. A. Sorochinsky, N. Voloshin, A. Markovsky, M. Belik, N. Yasuda, H. Uekusa, T. Ono, D.O. Berbasov, and V.A. Soloshonok J. Org. Chem. 68 2003 7448
69. K. Funabiki, M. Nagamori, S. Goushi, and M. Matsui Chem. Commun. 2004 1928
70. S. Fustero, D. Jimenez, J.F. Sanz-Cervera, M. Sanchez-Rosello, E. Esteban, and A. Simon-Fuentes Org. Lett. 7 2005 3433
71. F. Huguenot, and T.J. Brigaud Org. Chem. 71 2006 2159
72. S. Fustero, C.D. Pozo, S. Catalan, J. Aleman, A. Parra, V. Marcos, and J.L. G. Ruano Org. Lett. 11 2009 641
73. H. Mei, Y. Xiong, J. Han, and Y. Pan Org. Biomol. Chem. 9 2011 1402
74. V.A. Soloshonok, C. Cai, V.J. Hruby, L.V. Meervelt, and N. Mischenko Tetrahedron 55 1999 12031
75. A. Viso, R. Fernández de La Pradilla, A. García, and A. Flores Chem. Rev. 105 2005 3167
76. A. Viso, R. Fernández de La Pradilla, A. García, and A. Flores Chem. Rev. 111 2011 PR1
77. V.A. Soloshonok, D.V. Avilov, V.P. Kukhar, L.V. Meervelt, and N. Mischenko Tetrahedron Lett. 38 1997 4671
78. H.B. Xie, J.T. Zhu, Z.X. Chen, S. Li, and Y.M. Wu J. Org. Chem. 75 2010 7468
79. C. Xie, H.B. Mei, L.M. Wu, V.A. Soloshonok, J.L. Han, and Y. Pan Eur. J. Org. Chem. 2014 1445
80. T.K. Ellis, C.H. Martin, G.M. Tsai, H. Ueki, and V.A. Soloshonok J. Org. Chem. 68 2003 6208
81. J.L. Moore, S.M. Taylor, and V.A. Soloshonok ARKIVOC VI 2005 287
82. C. Xie, H. Mei, L. Wu, V.A. Soloshonok, J. Han, and Y. Pan RSC Adv. 4 2014 4763
83. V.A. Soloshonok, H. Ueki, R. Tiwari, C. Cai, and V.J. Hruby J. Org. Chem. 69 2004 4984
84. V.A. Soloshonok, C. Cai, and V.J. Hruby Tetrahedron Lett. 41 2000 135
85. V.A. Soloshonok, C. Cai, and V.J. Hruby Tetrahedron Lett. 41 2000 9645
86. V.A. Soloshonok, C. Cai, and V.J. Hruby Tetrahedron: Asymmetry 10 1999 4265
87. R. Budriesi, P. Ioan, A. Leoni, N. Pedemonte, A. Locatelli, M. Micucci, A. Chiarini, and L.J.V. Galietta J. Med. Chem. 54 2011 3885
88. N.U. Guzeldemirci, and O. Kucukbasmaci Eur. J. Med. Chem. 45 2010 63
89. A.H.M. Raeymaekers, F.T.N. Allewijn, J. Vandenberk, P.J.A. Demoen, T.T.T. Van Offenwert, and P.A.J. Janssen J. Med. Chem. 9 1966 545
90. H. Mei, C. Xie, L. Wu, V.A. Soloshonok, J. Han, and Y. Pan Org. Biomol. Chem. 11 2013 8018
91. B. Berk, G. Aktay, E. Yesilada, and M. Ertan Pharmazie 56 2001 613
92. B.S. Holla, K.N. Poojary, B. Kalluraya, and P.V. Gowda Farmaco 51 1996 7939
93. D.D.J. Cartwright, B.A.J. Clark, and H. McNab J. Chem. Soc., Perkin Trans. 1 2001 424
94. H.A.H. El- Sherif, A.M. Mahmoud, A.A.O. Sarhan, Z.A. Hozien, and O.M. A. Habib J. Sulfur Chem. 27 2006 65
95. H. Mei, Y. Xiong, C. Xie, V.A. Soloshonok, J. Han, and Y. Pan Org. Biomol. Chem. 12 2014 2108
96. V.A. Soloshonok, and D.O. Berbasov Chim. Oggi/Chem. Today 24 2006 44
97. V.A. Soloshonok, C. Roussel, O. Kitagawa, and A.E. Sorochinsky Chem. Soc. Rev. 41 2012 4180
98. A.E. Sorochinsky, J.L. Aceña, and V.A. Soloshonok Synthesis 45 2013 141
99. A.E. Sorochinsky, T. Katagiri, T. Ono, A. Wzorek, J.L. Aceña, and V.A. Soloshonok Chirality 25 2013 365
100. V.A. Soloshonok, and D.O. Berbasov J. Fluor. Chem. 127 2006 597
101. V.A. Soloshonok, H. Ueki, M. Yasumoto, S. Mekala, J.S. Hirschi, and D.A. Singleton J. Am. Chem. Soc. 129 2007 12112
102. H. Ueki, M. Yasumoto, and V.A. Soloshonok Tetrahedron: Asymmetry 21 2010 1396