Fluorinated aromatic ketones as nucleophiles in the asymmetric organocatalytic formation of C-C and C-N bonds: A facile route to the construction of fluorinated quaternary stereogenic centers

Chemistry - A European Journal

Volumn 17, Issue 13, 2011, Pages 3571-3574

  Zhao, Yujun ^a   Pan, Yuanhang ^a   Liu, Hongjun ^a   Yang, Yuanyong ^a   Jiang, Zhiyong ^b   Tan, Choon Hong ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b HENAN UNIVERSITY   (China)

Author keywords

amination; fluorine; Mannich reaction; organocatalysis; quaternary stereogenic center

Indexed keywords

AMINATION REACTION; AROMATIC KETONES; ENANTIOSELECTIVE; MANNICH REACTIONS; ORGANOCATALYSIS; ORGANOCATALYTIC; QUATERNARY STEREOGENIC CENTER; STEREOGENIC CENTERS;

AROMATIC COMPOUNDS; CATALYSIS; FLUORINE; KETONES; NUCLEOPHILES; RATE CONSTANTS; REACTION KINETICS;

AMINES;

FLUORINATED HYDROCARBON; KETONE; MANNICH BASE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; STEREOISOMERISM; SYNTHESIS;

AMINATION; CATALYSIS; HALOGENATION; HYDROCARBONS, FLUORINATED; KETONES; MANNICH BASES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79952611574     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003761     Document Type: Article

References (95)

1. Catalytic Asymmetric Synthesis (Ed.:, I. Ojima,), Wiley-Blackwell, New York, 2010
2. A. Berkessel, H. Groger, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005.
3. A. Ting, J. M. Goss, N. T. McDougal, S. E. Schaus, Top. Curr. Chem. 2009, 291, 145-200
4. M. Nielsen, C. B. Jacobsen, N. Holub, M. W. Paixão, K. A. Jørgensen, Angew. Chem. 2010, 122, 2726-2738
5. Angew. Chem. Int. Ed. 2010, 49, 2668-2679.
6. S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716
7. B. List, Tetrahedron 2002, 58, 5573-5590
8. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580-591
9. B. List, Chem. Commun. 2006, 819-824.
10. G. Zhong, J. Fan, C. F. Barbas III, Tetrahedron Lett. 2004, 45, 5681-5684
11. X.-Y. Xu, Y.-J. Wang, L.-F. Cun, L.-Z. Gong, Tetrahedron: Asymmetry 2007, 18, 237-242
12. X.-Y. Xu, Y.-Z. Wang, L.-Z. Gong, Org. Lett. 2007, 9, 4247-4249
13. T. Hoffmann, G. Zhong, B. List, D. Shabat, J. Anderson, S. Gramatikova, R. A. Lerner, C. F. III. Barbas, J. Am. Chem. Soc. 1998, 120, 2768-2779.
14. L. Yue, W. Du, Y.-K. Liu, Y.-C. Chen, Tetrahedron Lett. 2008, 49, 3881-3884
15. X. Jiang, Y. Zhang, A. S. C. Chan, R. Wang, Org. Lett. 2009, 11, 153-156
16. C. G. Kokotos, G. Kokotos, Adv. Synth. Catal. 2009, 351, 1355-1362
17. K. Liu, H.-F. Cur, J. Nie; K.-Y. Dong, X.-J. Li, J.-A. Ma, Org. Lett. 2007, 9, 923-925
18. K.-Y. Dong, X.-J. Li, J.-A. Ma, Org. Lett. 2007, 9, 923-925
19. Q. Guo, M. Bhanushali, C.-G. Zhao, Angew. Chem. 2010, 122, 9650-9654
20. Angew. Chem. Int. Ed. 2010, 49, 9460-9464.
21. D. Leow, C.-H. Tan, Chem. Asian J. 2009, 4, 488-507
22. D. Leow, C.-H. Tan, Synlett 2010, 1589-1605
23. C. Palomo, M. Oiarbide, R. Lõpez, Chem. Soc. Rev. 2009, 38, 632-653
24. J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724.
25. D. A. Alonso, S. Kitagaki, N. Utsumi, C. F. Barbas III, Angew. Chem. 2008, 120, 4664-4667
26. Angew. Chem. Int. Ed. 2008, 47, 4588-4591
27. N. Utsumi, S. Kitagaki, C. F. Barbas III, Org. Lett. 2008, 10, 3405-3408
28. M. C. Kohler, J. M. Yost, M. R. Garnsey, D. M. Coltart, Org. Lett. 2010, 12, 3376-3379
29. M. Terada, D. Tsushima, M. Nakano, Adv. Synth. Catal. 2009, 351, 2817-2821
30. C. Guo, M.-X. Xue, M.-K. Zhu, L.-Z. Gong, Angew. Chem. 2008, 120, 3462-3465
31. Angew. Chem. Int. Ed. 2008, 47, 3414-3417
32. F. Marini, S. Sternativo, F. D. Verme, L. Testaferri, M. Tiecco, Adv. Synth. Catal. 2009, 351, 103-106
33. T.-Y. Liu, R. Li, Q. Chai, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Chem. Eur. J. 2007, 13, 319-327
34. S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120-8121
35. X. Liu, H. Li, L. Deng, Org. Lett. 2005, 7, 167-169
36. X. Wang, M. Kitamura, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 1038-1039
37. H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948-8949
38. J. Wang, L. Zu, W. Jiang, W. Duan, W. Wang, J. Am. Chem. Soc. 2006, 128, 12652-12653
39. H. W. Moon, D. Y. Kim, Tetrahedron Lett. 2010, 51, 2906-2908
40. A. Prieto, N. Halland, K. A. Jørgensen, Org. Lett. 2005, 7, 3897-3900
41. D. Uraguchi, K. Koshimoto, T. Ooi, J. Am. Chem. Soc. 2008, 130, 10878-10879.
42. T.-Y. Liu, H.-L. Cui, Y. Zhang, K. Jiang, W. Du, Z.-Q. He, Y.-C. Chen, Org. Lett. 2007, 9, 3671-3674.
43. B. Wang, F. Wu, X. Liu, L. Deng, J. Am. Chem. Soc. 2007, 129, 768-769
44. Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2006, 128, 3928-3930
45. J.-H. Lee, D. Y. Kim, Adv. Synth. Catal. 2009, 351, 1779-1782
46. S. M. Kim, J. H. Lee, D. Y. Kim, Synlett 2008, 2659-2662
47. S.-L. Zhao, C.-W. Zheng, H.-F. Wang, G. Zhao, Adv. Synth. Catal. 2009, 351, 2811-2816.
48. Fluorine in Medicinal Chemistry and Chemical Biology (Ed.:, I. Ojima,), Wiley-Blackwell, New York, 2009.
49. For a recent review of the organocatalytic formation of quaternary stereocenters, see:, M. Bella, T. Gasperi, Synthesis 2009, 1583-1614.
50. P. M. Pihko, Angew. Chem. 2006, 118, 558-561
51. Angew. Chem. Int. Ed. 2006, 45, 544-547
52. G. K. S. Prakash, P. Beier, Angew. Chem. 2006, 118, 2228-2230
53. Angew. Chem. Int. Ed. 2006, 45, 2172-2174
54. V. A. Brunet, D. O'Hagan, Angew. Chem. 2008, 120, 1198-1201
55. Angew. Chem. Int. Ed. 2008, 47, 1179-1182
56. J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119-6146
57. N. Shibaba, T. Ishimaru, S. Nakamura, T. Toru, J. Fluorine Chem. 2007, 128, 469- 483
58. H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147-1155
59. S. Lectard, Y. Hamashima, M. Sodeoka, Adv. Synth. Catal. 2010, 352, 2708-2732
60. C. Bobbio, V. Gouverneur, Org. Biomol. Chem. 2006, 4, 2065-2075
61. S. Brandes, B. Niess, M. Bella, A. Prieto, J. Overgaard, K. A. Jørgensen, Chem. Eur. J. 2006, 12, 6039-6052.
62. H. Li, S. Zhang, C. Yu, X. Song, W. Wang, Chem. Commun. 2009, 2136-2138
63. X. Han, J. Luo, C. Liu, Y. Lu, Chem. Commun. 2009, 2044-2046
64. X. Han, J. Kwiatkowski, F. Xue, K-W. Huang, Y. Lu, Angew. Chem. 2009, 121, 7740-7743
65. Angew. Chem. Int. Ed. 2009, 48, 7604-7607
66. Y. Oh, S. M. Kim, D. Y. Kim, Tetrahedron Lett. 2009, 50, 4674-4676
67. C. Ding, K. Maruoka, Synlett 2009, 664-666
68. H.-F. Cui, Y.-Q. Yang, Z. Chai, P. Li, C.-W. Zheng, S.-Z. Zhu, G. Zhao, J. Org. Chem. 2010, 75, 117-122
69. F. Ullah, G-L. Zhao, Deiana, L. M. Zhu, P. Dziedzic, I. Ibrahem, P. Hammar, J. Sun, A. Cõrdova, Chem. Eur. J. 2009, 15, 10013-10017
70. T. Furukawa, N. Shibata, S. Mizuta, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 8171-8174
71. Angew. Chem. Int. Ed. 2008, 47, 8051-8054
72. S. Mizuta, N. Shibata, Y. Goto, T. Furukawa, S. Nakamura, T. Toru, J. Am. Chem. Soc. 2007, 129, 6394-6395
73. G. K. S. Prakash, F. Wang, T. Stewart, T. Mathew, G. A. Olah, Proc. Natl. Acad. Sci. USA 2009, 106, 4090-4094
74. S. Arai, M. Oku, T. Ishida, T. Shioiri, Tetrahedron Lett. 1999, 40, 6785-6789
75. B. Thierry, T. Perrard, C. Audouard, J.-C. Plaquevent, D. Cahard, Synthesis 2001, 1742-1746
76. X. Han, F. Zhong, Y. Lu, Adv. Synth. Catal. 2010, 352, 2778-2782.
77. Z. Yu, X. Liu, L. Zhou, L. Lin, X. Feng, Angew. Chem. 2009, 121, 5297-5300
78. Angew. Chem. Int. Ed. 2009, 48, 5195-5198
79. H. Ube, M. Shimada, M. Terada, Angew. Chem. 2010, 122, 1902-1905
80. Angew. Chem. Int. Ed. 2010, 49, 1858-1861
81. T. Misaki, G. Takimoto, T. Sugimura, J. Am. Chem. Soc. 2010, 132, 6286-6287
82. S. Dong, X. Liu, X. Chen, F. Mei, Y. Zhang, B. Gao, L. Lin, X. Feng, J. Am. Chem. Soc. 2010, 132, 10650-10651.
83. Z. Jiang, Y. Pan, Y. Zhao, T. Ma, R. Lee, Y. Yang, K.-W. Huang, M. W. Wang, C.-H. Tan, Angew. Chem. 2009, 121, 3681-3685
84. Angew. Chem. Int. Ed. 2009, 48, 3627-3631
85. Y. Pan, Y. Zhao, T. Ma, Y. Yang, H. Liu, Z. Jiang, C.-H. Tan, Chem. Eur. J. 2009, 15, 779-782.
86. The reaction between nonfluorinated tetralone and 3 a was very slow under the same reaction conditions.
87. J. Y. Mang, D. G. Kwon, D. Y. Kim, J. Fluorine Chem. 2009, 130, 259-262
88. D. P. Huber, K. Stanek, A. Togni, Tetrahedron: Asymmetry 2006, 17, 658-664.
89. R. D. Little, R. G. Venegas, Org. Syn. 1983, 61, 17-20
90. L. A. Carpino, B. A. Carpino, C. A. Giza, P. H. Terry, Org. Syn. 1964, 44, 15-17
91. L. A. Carpino, P. J. Crowley, Org. Syn. 1964, 44, 18-20.
92. The Flavonoids: Advances in Research Since 1980 (Ed.:, J. B. Harborne,), Chapman and Hall, New York, 1994
93. Flavonoid in Biology and Medicine III: Proceedings of 3rd International Symposium on Flavonoids in Biology Medicine (Ed.:, N. P. Das,), National University of Singapore, Singapore, 1989.
94. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797-5815
95. J. M. M. Verkade, L. J. C. Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Ruties, Chem. Soc. Rev. 2008, 37, 29-41.