Highly efficient catalytic asymmetric Sulfa-Michael addition of thiols to trans-4,4,4-trifluorocrotonoylpyrazole

Advanced Synthesis and Catalysis

Volumn 354, Issue 6, 2012, Pages 1141-1147

  Dong, Xiu Qin ^a   Fang, Xin ^a   Tao, Hai Yan ^a   Zhou, Xiang ^a   Wang, Chun Jiang ^a,b  

^a WUHAN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

4,4,4 trifluorocrotonamide; amine thiourea catalysts; asymmetric catalysis; pyrazoles; sulfa Michael addition; trifluoromethyl group

Indexed keywords

EID: 84859992629     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100899     Document Type: Article

References (99)

1. Fluorine in Medicinal Chemistry and Chemical Biology, (Ed.:, I. Ojima,), Wiley-Blackwell, New York, 2009
2. J.-P. Bégué, D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, John Wiley & Sons, Inc., New York, 2008
3. A. Tressaud, G. Haufe, Fluorine and Health-Molecular Imaging, Biomedical Materials and Pharmaceuticals, Elsevier, Amsterdam, 2008
4. A. M. Thayer, Chem. Eng. News 2006, 84, 15.
5. Fluorine Containing Amino Acids-Synthesis and Properties, (Eds.:, V.P. Kukhar, V.A. Soloshonok,), Wiley, Chichester, 1995
6. K. Uneyama, in: Enantiocontrolled Synthesis of Fluoro-Organic Compounds, (Ed.:, V.A. Soloshonok,), Wiley, Chichester, 1999, Chapter 12
7. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320
8. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1
9. R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev. 2008, 37, 1727
10. J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev. 2011; 111, 455
11. G. F. Georgii, Fluorine-Containing Heterocycles. Part I. Synthesis by Intramolecular Cyclization, in: Advances in Heterocyclic Chemistry, (Ed.:, A.R. Katritzky,), Elsevier, Amsterdam, 2004; for a recent special issue on organofluorine chemistry, see
12. Adv. Synth. Catal. 2010, 352, 2677.
13. A. Nudelman, The Chemistry of Optically Active Sulfur Compounds, Gordon and Breach, New York, 1984
14. Sulphur-Containing Drugs and Related Organic Compounds, (Ed.:, L.A. Damani,), Wiley, New York, 1989
15. Organosulfur Chemistry in Asymmetric Synthesis, (Eds.:, T. Toru, C. Bolm,), Wiley-VCH, Weinheim, Germany, 2008
16. Chiral Sulfur Ligands: Asymmetric Catalysis, (Ed.:, H. Pellissier,), Cambridge, U.K, 2009
17. J. Clayden, P. MacLellan, Beilstein J. Org. Chem. 2011, 7, 582.
18. For a comprehensive review on asymmetric sulfa-Michael additions, see:, D. Enders, K. Lüttgen, A. A. Narine, Synthesis 2007, 959.
19. For examples of organometallic-catalyzed Michael addition of thiols, see
20. K. Nishimura, M. Ono, Y. Nagaoka, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 12974
21. E. Emori, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 4043
22. S. Kanemasa, Y. Oderaotoshi, E. Wada, J. Am. Chem. Soc. 1999, 121, 8675
23. E. Emori, T. Iida, M. Shibasaki, J. Org. Chem. 1999, 64, 5318
24. S. Kobayashi, C. Ogawa, M. Kawamura, M. Sugiura, Synlett 2001, 983
25. K. Matsumoto, A. Watanabe, T. Uchida, K. Ogi, T. Katsuki, Tetrahedron Lett. 2004, 45, 2385
26. A. M. M. Abe, S. J. K. Sauerland, A. M. P. Koskinen, J. Org. Chem. 2007, 72, 5411
27. M. Kawatsura, Y. Komatsu, M. Yamamoto, S. Hayase, T. Itoh, Tetrahedron 2008, 64, 3488
28. A. BÇdoiu, G. Bernardinelli, C. Besnard, E. P. Kündig, Org. Biomol. Chem. 2010, 8, 193.
29. For examples of organocatalyzed asymmetric sulfa-Michael addition, see
30. H. Hiemstra, H. Wynberg, J. Am. Chem. Soc. 1981, 103, 417
31. P. McDaid, Y. G. Chen, L. Deng, Angew. Chem. 2002, 114, 348
32. Angew. Chem. Int. Ed. 2002, 41, 338
33. T. C. Wabnitz, J. B. Spencer, Org. Lett. 2003, 5, 2141
34. B.-J. Li, L. Jiang, M. Liu, Y.-C. Chen, L.-S. Ding, Y. Wu, Synlett 2005, 603
35. H. Li, J. Wang, L.-S. Zu, W. Wang, Tetrahedron Lett. 2006, 47, 2585
36. Y. Liu, B.-F. Sun, B.-M. Wang, M. Wakem, L. Deng, J. Am. Chem. Soc. 2009, 131, 418
37. K. Kimmel, M. T. Robak, J. A. Ellman, J. Am. Chem. Soc. 2009, 131, 8754
38. N. K. Rana, S. Selvakumar, V. K. Singh, J. Org. Chem. 2010, 75, 2089
39. D. Enders, K. Hoffman, Eur. J. Org. Chem. 2009, 1665
40. J. Sun, G. C. Fu, J. Am. Chem. Soc. 2010, 132, 4568
41. D. Leow, S. Lin, S. K. Chittimlla, X. Fu, C.-H. Tan, Angew. Chem. 2008, 120, 5723
42. Angew. Chem. Int. Ed. 2008, 47, 5641
43. Y.-H. Hui, J. Jiang, W.-T. Wang, W.-L. Chen, Y.-F. Cai, L.-L. Lin, X.-H. Liu, X.-M. Feng, Angew. Chem. 2010, 122, 4386
44. Angew. Chem. Int. Ed. 2010, 49, 4290
45. X.-F. Wang, Q.-L. Hua, Y. Cheng, X.-L. An, Q.-Q. Yang, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2010, 122, 8557
46. Angew. Chem. Int. Ed. 2010, 49, 8379
47. X. Tian, C. Cassani, Y. Liu, A. Moran, A. Urakawa, P. Galzerano, E. Arceo, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 17934.
48. For examples of organocatalytic tandem reactions of thiols, see
49. M. Marigo, T. Schulte, J. Franzén, K. A. Jrgensen, J. Am. Chem. Soc. 2005, 127, 15710
50. S. Brandau, E. Maerten, K. A. Jgensen, J. Am. Chem. Soc. 2006, 128, 14986
51. W. Wang, H. Li, J. Wang, L.-S. Zu, J. Am. Chem. Soc. 2006, 128, 10354
52. L.-S. Zu, J. Wang, H. Li, H.-X. Xie, W. Jiang, W. Wang, J. Am. Chem. Soc. 2007, 129, 1036
53. L.-S. Zu, H.-X. Xie, H Li, J. Wang, W. Jiang, W. Wang, Adv. Synth. Catal. 2007, 349, 1882
54. G.-L. Zhao, J. Vesely, R. Rios, I. Ibrahem, H. Sundén, A. Cõrdova, Adv. Synth. Catal. 2008, 350, 237
55. R. Dodda, J. J. Goldman, T. Mandal, C.-G. Zhao, G. A. Broker, E. R. T. Tiekink, Adv. Synth. Catal. 2008, 350, 537.
56. M. Sani, G. Candiani, F. Pecker, L. Malpezzi, M. Zanda, Tetrahedron Lett. 2005, 46, 2393
57. D. Enders, Z.-X. Chen, Lett. Org. Chem. 2005, 2, 156
58. N. M. Karimova, A. A. Glazkov, A. V. Ignatenko, A. F. Kolomiets, Russ. Chem. Bull. Int. Ed. 2003, 52, 1621
59. T. Kitazume, K. Murata, J. Fluorine Chem. 1988, 39, 75.
60. X.-Q. Dong, X. Fang, C.-J. Wang, Org. Lett. 2011, 13, 4426.
61. J. Leroy, N. Fischer, C. Wakselman, J. Chem. Soc. Perkin Trans. 1 1990, 1281
62. B. C. Hamper, Org. Synth. 1998, 49, 1430.
63. B.-L. Wang, F. Yu, X.-L. Qiu, Z. Jiang, F.-L. Qing, J. Fluorine Chem. 2006, 127, 580.
64. For selected examples, see
65. D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc. 2007, 129, 10029
66. M. P. Sibi, K. Itoh, J. Am. Chem. Soc. 2007, 129, 8064
67. S. Matsunaga, T. Kinoshita, S. Okada, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 7559
68. J. K. Myers, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 8959
69. A. Baschieri, L. Bernardi, A. Ricci, S. Suresh, M. P. A. Adamo, Angew. Chem. 2009, 121, 9506
70. Angew. Chem. Int. Ed. 2009, 48, 9342
71. D. A. Evans, J. S. Johnson, J. Am. Chem. Soc. 1998, 120, 4895
72. D. A. Evans, K. R. Fandrick, H.-J. Song, J. Am. Chem. Soc. 2005, 127, 8942.
73. For reviews on bifunctional organocatalysis, see
74. S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701
75. Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299
76. T. Marcelli, J. H. V. Maarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 7658
77. Angew. Chem. Int. Ed. 2006, 45, 7496
78. S. J. Connon, Chem. Eur. J. 2006, 12, 5418
79. A.-G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
80. H. Miyabe, Y. Takemoto, Bull. Chem. Soc. Jpn. 2008, 81, 785.
81. C. Kashima, H. Harada, I. Kita, I. Fukuchi, A. Hosomi, Synthesis 1994, 61.
82. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672
83. T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119
84. B. Vakulya, S. Varga, A. Csámpai, T. Soõs, Org. Lett. 2005, 7, 1967
85. T. Marcelli, J. H. vanMaarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 7658
86. Angew. Chem. Int. Ed. 2006, 45, 7496
87. S. J. Connon, Chem. Commun. 2008, 2499.
88. C.-J. Wang, Z.-H. Zhang, X.-Q. Dong, X.-J. Wu, Chem. Commun. 2008, 1431
89. Z.-H. Zhang, X.-Q. Dong, D. Chen, C.-J. Wang, Chem. Eur. J. 2008, 14, 8780
90. C.-J. Wang, X.-Q. Dong, Z.-H. Zhang, Z.-Y. Xue, H.-L. Teng, J. Am. Chem. Soc. 2008, 130, 8606
91. X.-Q. Dong, H.-L. Teng, C.-J. Wang, Org. Lett. 2009, 11, 1265
92. X.-Q. Dong, H.-L. Teng, M.-C. Tong, H. Huang, H.-Y. Tao, C.-J. Wang, Chem. Commun. 2010, 46, 6840.
93. F. Zhang, Z.-J. Liu, J.-T. Liu, Tetrahedron 2010, 66, 6864.
94. Racemic syn-2-trifluoromethylthiochroman-4-ol 9aa is a known compound, hence the second generated stereogenic center was assigned as the S configuration, see:, B. I. Usachev, M. A. Shafeev, V. Y. Sosnovskikh, Russ. Chem. Bull. Int. Ed. 2006, 55, 523.
95. A. Hamza, G. Schubert, T. Soõs, I. Pápai, J. Am. Chem. Soc. 2006, 128, 13151
96. T.-Y. Liu, J. Long, B.-J. Li, L. Jiang, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2006, 4, 2097
97. F.-Z. Peng, Z.-H. Shao, B.-M. Fan, H. Song, G.-P. Li, H.-B. Zhang, J. Org. Chem, 2008, 73, 5202
98. A.-D. Lu, P. Gao, Y. Wu, Y.-M. Wang, Z.-H. Zhou, C.-C. Tang, Org. Biomol. Chem. 2009, 7, 3141
99. X.-X. Jiang, G. Zhang, D. Fu, Y.-M. Cao, F.-F. Shen, R. Wang, Org. Lett. 2010, 12, 1544.