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http://dx.doi.org/10.5012/bkcs.2011.32.4.1195

Asymmetric Mannich-type Reactions of Fluorinated Ketoesters with Binaphthyl-Modified Thiourea Catalysts  

Kang, Young-Ku (Department of Chemistry, Soonchunhyang University)
Yoon, Sung-Je (Department of Chemistry, Soonchunhyang University)
Kim, Dae-Young (Department of Chemistry, Soonchunhyang University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.4, 2011 , pp. 1195-1200 More about this Journal
Abstract
The catalytic enantioselective Mannich-type reaction promoted by chiral binaphthyl-modified bifunctional organocatalysts is described. The treatment of ${\alpha}$-fluoro-${\beta}$-ketoesters with N-Boc imines under mild reaction conditions afforded the corresponding ${\beta}$-aminated ${\alpha}$-fluoro-${\beta}$-ketoesters with excellent enantioselectivities (up to 98% ee).
Keywords
Mannich reaction; Asymmetric catalysis; Bifunctional organocatalyst; ${\alpha}$-Fluoro-${\beta}$-ketoesters; N-Boc imines;
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1 Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2091.   DOI   ScienceOn
2 Kwon, B. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1441.   DOI   ScienceOn
3 Yoon, S. J.; Kang, Y. K.; Kim, D. Y. Synlett 2011, 420.
4 Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2011, 52, 2356.   DOI   ScienceOn
5 Brunner, H.; Buegler, J.; Nuber, B. Tetrahedron: Asymmetry 1995, 6, 1699.   DOI   ScienceOn
6 Oliva, C. G.; Silva, A. M. S.; Resende, D. I. S. P.; Paz, F. A. A.; Cavaleiro, J. A. S. Eur. J. Org. Chem. 2010, 3449.
7 Arai, T.; Watanabe, M.; Fujiwara, A.; Yokoyama, N.; Yanagisawa, A. Angew. Chem. Int. Ed. 2006, 45, 6978.
8 Arai, T.; Watanabe, M.; Yanagisawa, Org. Lett. 2007, 9, 3595.   DOI   ScienceOn
9 Liu, Q.-Z.; Wang, X.-L.; Luo, S.-W.; Zheng, B. L.; Qin, D.-B.; Tetrahedron Lett. 2008, 49, 7434.   DOI   ScienceOn
10 Jiang, Z.; Pan, Y.; Zhao, Y.; Ma, T.; Lee, R.; Yang, Y.; Huang, K.-W.; Wong, M. W.; Tan, C.-H. Angew. Chem., Int. Ed. 2009, 48, 3627.   DOI   ScienceOn
11 Pan, Y.; Zhao, Y.; Ma, T.; Yang, Y.; Liu, H.; Jiang, Z.; Tan, C.-H. Chem. Eur. J. 2010, 16, 779.   DOI   ScienceOn
12 Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299.   DOI   ScienceOn
13 Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933.   DOI   ScienceOn
14 Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897.   DOI   ScienceOn
15 Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565.   DOI   ScienceOn
16 Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135.
17 Cho, M. J.; Kang, Y. K.; Lee, N. R.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2191.   DOI   ScienceOn
18 Kim, S. M.; Kang, Y. K.; Cho, M. J.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2435.   DOI   ScienceOn
19 Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821.
20 Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2093   DOI   ScienceOn
21 Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2036.   DOI   ScienceOn
22 Mang, J. Y.; Kwon, D. G.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 249.   DOI   ScienceOn
23 Kang, S. H.; Kang, Y. K.; Kim, D. Y. Tetrahedron 2009, 65, 5676.   DOI   ScienceOn
24 Sikert, M.; Schneider, C. Angew. Chem., Int. Ed. 2008, 47, 3631.   DOI   ScienceOn
25 Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847.   DOI   ScienceOn
26 Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659.
27 Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527.   DOI   ScienceOn
28 Itoh, J.; Fuchibe, K.; Akiyama, T. Synthesis 2008, 1319.
29 Kobayashi, S.; Yazaki, R.; Seki, K.; Ueno, M. Tetrahedron 2007, 63, 8425.   DOI   ScienceOn
30 Saruhashi, K.; Kobayashi, S. J. Am. Chem. Soc. 2006, 128, 11232.   DOI   ScienceOn
31 Kobayashi, S.; Ueno, M.; Saito, S.; Mizuki, Y.; Ishitani, H.; Yamashita, Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5476.   DOI   ScienceOn
32 Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.   DOI   ScienceOn
33 Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.   DOI   ScienceOn
34 Hamashima, Y.; Sasamoto, N.; Umebayashi, N.; Sodeoka, M. Chem. Asian J. 2008, 3, 1443.   DOI   ScienceOn
35 Chen, Z.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 2170.   DOI   ScienceOn
36 Kobayashi, S.; Gustafsson, T.; Shimizu, Y.; Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8, 4923.   DOI   ScienceOn
37 Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem., Int. Ed. 2005, 44, 1525.   DOI   ScienceOn
38 Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734.   DOI   ScienceOn
39 Kim, E. J.; Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1437.   DOI   ScienceOn
40 Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779.   DOI   ScienceOn
41 Lee, J. H.; Kim, D. Y. Synthesis 2010, 1860.
42 Han, X.; Kwiatkowski, J.; Xue, F.; Huang, K.-W.; Lu, Y. Angew. Chem., Int. Ed. 2009, 48, 7604.   DOI   ScienceOn
43 He, R.; Wang, X.; Hashimoto, T.; Maruoka, K. Angew. Chem. Int. Ed. 2008, 47, 9466.   DOI   ScienceOn
44 Mang, J. Y.; Kwon, D. G.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 259.   DOI   ScienceOn
45 Han, X.; Luo, J.; Liu, C.; Lu, Y. Chem. Commun. 2009, 2044.
46 Li, H.; Zhang, S.; Yu, C.; Song, X.; Wang, W. Chem. Commun. 2009, 2136.
47 Oh, Y.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4674.   DOI   ScienceOn
48 Ishimaru, T.; Ogawa, S.; Tokunaga, E.; Nakamura, S.; Shibata, N. J. Fluorine Chem. 2009, 130, 1049.   DOI   ScienceOn
49 Cui, H.-F.; Yang, Y.-Q.; Chai, Z.; Li, P.; Zheng, C.-W.; Zhu, S.-Z. J. Org. Chem. 2010, 75, 117.   DOI   ScienceOn
50 Fukuzumi, T.; Shibata, N.; Sugiura, M.; Yasui, H.; Nakamura, S.; Toru, T. Angew. Chem. Int. Ed. 2006, 45, 4973.   DOI   ScienceOn
51 Mizuta, S.; Shibata, N.; Goto, Y.; Furukawa, T.; Nakamura, S.; Toru, T. J. Am. Chem. Soc. 2007, 129, 6394.   DOI   ScienceOn
52 Furukawa, T.; Shibata, N.; Mizuta, S.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem. Int. Ed. 2008, 47, 8051.   DOI   ScienceOn
53 Ting, A.; Schaus, S. E. Eur. J. Org. Chem. 2007, 5797.
54 Moon, H. W.; Cho, M. J.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4896.   DOI   ScienceOn
55 Furukawa, T.; Goto, Y.; Kawazoe, J.; Tokunaga, E.; Nakamura, S.; Yang, Y.; Du, H.; Kakehi, A.; Shiro, M.; Shibata, N. Angew. Chem. Int. Ed. 2010, 49, 1642.   DOI   ScienceOn
56 Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29.   DOI   ScienceOn
57 Marques, M. M. B. Angew. Chem. Int. Ed. 2006, 45, 348.   DOI   ScienceOn
58 Cordova, A. Acc. Chem. Res. 2004, 37, 102.   DOI   ScienceOn
59 Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359.   DOI   ScienceOn
60 Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545.   DOI   ScienceOn
61 Hamashima, Y.; Yagi, K.; Takano, H.; Tamás, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530.   DOI   ScienceOn
62 Ma, J.-A.; Cahard, D. Tetrahedron: Asymmetry 2004, 15, 1007.   DOI   ScienceOn
63 Shibata, N.; Ishimaru, T.; Nagai, T.; Kohno. J.; Toru, T. Synlett 2004, 1703.
64 Bernardi, L.; Jorgensen, K. A. Chem. Commun. 2005, 1324.
65 Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309.   DOI   ScienceOn
66 Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115.   DOI   ScienceOn
67 Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem. Int. Ed. 2008, 47, 4157.   DOI   ScienceOn
68 Kim, D. Y.; Kim, S. M.; Koh, K. O.; Mang, J. Y. Bull. Korean Chem. Soc. 2003, 24, 1425.   DOI   ScienceOn
69 Lee, N. R.; Kim, S. M.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 829.   DOI   ScienceOn
70 Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783.   DOI   ScienceOn
71 Nichols, P. J.; DeMattei, J. A.; Barnett, B. R.; LeFur, N. A.; Chuang, T.-H.; Piscopio, A. D.; Koch, K. Org. Lett. 2006, 8, 1495.   DOI   ScienceOn
72 Kwon, B. K.; Kim, S. M.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 759.   DOI   ScienceOn
73 Companyo, X.; Hejnova, M.; Kamlar, M.; Vesely, J.; Moyano, A.; Rios, R. Tetrahedron Lett. 2009, 50, 5051.
74 Nakamura, M.; Hajra, A.; Endo, K.; Nakamura, E. Angew. Chem. Int. Ed. 2005, 44, 7248.   DOI   ScienceOn
75 Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu, M. Organofluorine Compounds: Chemistry and Applications; Springer-Verlag: Berlin, 2000.
76 Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.   DOI   ScienceOn
77 Enantiocontrolled Synthesis of Fluoro-organic Compounds; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999.
78 Ramachandran, P. V., Ed.; Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions; ACS Symposium Series 746; American Chemical Society: Washington, DC, 2000.
79 Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1.   DOI   ScienceOn
80 Ibrahim, H.; Togni, A. Chem. Commun. 2004, 1147.
81 Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1.   DOI   ScienceOn
82 Prakash, G. K. S.; Beier, P. Angew. Chem. Int. Ed. 2006, 45, 2172.   DOI   ScienceOn
83 France, S.; Weatherwax, A.; Lectka, T. Eur. J. Org. Chem. 2005, 475.
84 Oestreich, M. Angew. Chem. Int. Ed. 2005, 44, 2324.   DOI   ScienceOn
85 Pihko, P. M. Angew. Chem. Int. Ed. 2006, 45, 544.   DOI   ScienceOn
86 Bobbio, C.; Gouverneur, V. Org. Biomol. Chem. 2006, 4, 2065.   DOI   ScienceOn
87 Shibata, N.; Ishimaru, T.; Nakamura, S.; Toru, T. J. Fluorine Chem. 2007, 128, 469.   DOI   ScienceOn
88 Brunet, V. A.; O’Hagan, D. Angew. Chem. Int. Ed. 2008, 47, 1179.   DOI   ScienceOn
89 Smits, R.; Cadicamo, C. D.; Burger, K.; Koksch, B. Chem. Soc. Rev. 2008, 37, 1727.   DOI   ScienceOn
90 Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917.   DOI   ScienceOn
91 Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.   DOI   ScienceOn
92 Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II; American Chemical Society: Washington, DC, 1995.
93 Kirk, K. L. J. J. Fluorine Chem. 2006, 127, 1013.   DOI   ScienceOn
94 Isanobor, C.; O’Hagan, D. J. Fluorine Chem. 2006, 127, 303.   DOI   ScienceOn
95 Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.   DOI   ScienceOn