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http://dx.doi.org/10.5012/bkcs.2007.28.12.2435

Catalytic Enantioselective Fluorination Reactions of α-Cyano Acetates and α-Cyanophosphonates Using Chiral Palladium Complexes  

Kim, Sun-Mi (Department of Chemistry, Soonchunhyang University)
Kang, Young-Ku (Department of Chemistry, Soonchunhyang University)
Cho, Min-Je (Department of Chemistry, Soonchunhyang University)
Mang, Joo-Yang (Department of Chemistry, Soonchunhyang University)
Kim, Dae-Young (Department of Chemistry, Soonchunhyang University)
Publication Information
Bulletin of the Korean Chemical Society / v.28, no.12, 2007 , pp. 2435-2441 More about this Journal
Abstract
The catalytic enantioselective electrophilic fluorinations of active methane compounds promoted chiral palladium complexes have been developed. Treatment of α-cyano acetates and α-cyanoalkylphosphonates with N-fluorobenzenesulfonimide as the fluorine source under mild reaction conditions afforded the corresponding α-cyano-α-fluorinated adducts in high yields with excellent enantiomeric excesses (up to 99% ee). These reactions can be conducted in alcoholic solvents without any precaution to exclude water and moisture.
Keywords
Chiral palladium complexes; Electrophilic fluorination; Asymmetric catalysis; ${\alpha}$-Cyano acetates; ${\alpha}$-Cyanoalkylphosphonates;
Citations & Related Records
Times Cited By KSCI : 6  (Citation Analysis)
Times Cited By Web Of Science : 30  (Related Records In Web of Science)
Times Cited By SCOPUS : 28
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1 Li, K.; Hii, K. K. Chem. Commun. 2003, 1132-1133
2 Li, K.; Horton, P. N.; Hursthouse, M. B.; Hii, K. K. J. Organometallic Chem. 2003, 665, 250-257. For Pd(II) chemistry, see   DOI   ScienceOn
3 Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for 21st Century; John Willey & Son: Chichester, 2004. For a aquapalladium complex, see
4 Shimada, T.; Bajracharya, G. B.; Yamamoto, Y. Eur. J. Org. Chem. 2005, 59-62, and references cited therein
5 Kim, D. Y.; Oh, D. Y. Synth. Commun. 1987, 17, 953-957   DOI   ScienceOn
6 Kim, D. Y.; Oh, D. Y. Bull. Korean Chem. Soc. 1997, 18, 994-998
7 Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301   DOI   ScienceOn
8 Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, 2004
9 Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004
10 Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu, M. Organofluorine Compounds: Chemistry and Applications; Springer-Verlag: Berlin, 2000
11 Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996. For reviews
12 Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013-1029   DOI   ScienceOn
13 Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1-16   DOI   ScienceOn
14 Ibrahim, H.; Togni, A. Chem. Commun. 2004, 1147-1155
15 Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. 2000, 39, 4359-4362   DOI   ScienceOn
16 Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119- 6149   DOI   ScienceOn
17 France, S.; Weatherwax, A.; Lectka, T. Eur. J. Org. Chem. 2005, 475-479
18 Prakash, G. K. S.; Bier, P. Angew. Chem., Int. Ed. 2006, 45, 2172-2174   DOI   ScienceOn
19 Hamashima, Y.; Suzuki, T.; Shimura, Y.; Shimizu, T.; Umebayashi, N.; Tamura, T.; Sasamoto, N.; Sodeoka, M. Tetrahedron Lett. 2005, 46, 1447- 1450   DOI   ScienceOn
20 Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309-2311   DOI   ScienceOn
21 Bohm, H.-J.; Banmer, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Muller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637-643   DOI   ScienceOn
22 Kim, S. M.; Kang, Y. K.; Lee, K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2006, 27, 423-425   DOI   ScienceOn
23 Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135-1138
24 Isanbor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303-319   DOI   ScienceOn
25 Smart, B. E. J. Fluorine Chem. 2001, 109, 3-11   DOI   ScienceOn
26 Ismail, F. M. D. J. Fluorine Chem. 2002, 118, 27-33   DOI   ScienceOn
27 Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions; Ramachandran, P. V., Ed.; ACS Symposium Series 746; American Chemical Society: Washington, DC, 2000
28 Enantiocontrolled Synthesis of Fluoro-organic Compounds; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999. For review
29 Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661-692   DOI   ScienceOn
30 Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755   DOI   ScienceOn
31 Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431-12477   DOI   ScienceOn
32 Fugiwara, T.; Sasaki, M.; Omata, K.; Kabuto, C.; Kabuto, K.; Takeuchi, Y. Tetrahedron: Asymmetry 2004, 15, 555-563   DOI   ScienceOn
33 Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225-3228   DOI   ScienceOn
34 Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729   DOI   ScienceOn
35 Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547   DOI   ScienceOn
36 Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530-14531   DOI   ScienceOn
37 Ma, J.-A.; Cahard, D. Tetrahedron: Asymmetry 2004, 15, 1007-1011   DOI   ScienceOn
38 Shibata, N.; Ishimaru, T.; Nagai, T.; Kohno, J.; Toru, T. Synlett 2004, 1703-1706
39 Shibata, N.; Kohno, J.; Takai, K.; Ishimaru, T.; Nakamura, S.; Toru, T.; Kanemasa, S. Angew. Chem., Int. Ed. 2005, 44, 4204- 4207   DOI   ScienceOn
40 Cho, M. J.; Kang, Y. K.; Lee, N. R.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2191   DOI   ScienceOn
41 Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115-3117   DOI   ScienceOn
42 Park, E. J.; Kim, H. R.; Joung, C. W.; Kim, D. Y. Bull. Korean Chem. Soc. 2004, 25, 1451-1452   DOI   ScienceOn
43 Bernardi, L.; Jorgensen, K. A. Chem. Commun. 2005, 1324-1326
44 Kim, D. Y.; Choi, Y. J.; Park, H. Y.; Joung, C. U.; Koh, K. O.; Mang, J. Y.; Jung, K.-Y. Synth. Commun. 2003, 33, 435-443   DOI   ScienceOn
45 Steiner, D. D.; Mase, N.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2005, 44, 3706-3710   DOI   ScienceOn
46 Moriyama, K.; Hamashima, Y.; Sodeoka, M. Synlett 2007, 1139-1142
47 Enders, D.; Huttl, M. R. M. Synlett 2005, 991-993
48 Marigo, M.; Fielenbach, D.; Braunton, A.; Kjaersgaard, A.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 3703-3706   DOI   ScienceOn
49 Beeson, T. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 8826-8828   DOI   ScienceOn
50 Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051- 15053   DOI   ScienceOn
51 Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions; Ramachandran, P. V., Ed.; ACS Symposium Series 746; American Chemical Society: Washington, DC, 2000
52 Enantiocontrolled Synthesis of Fluoro-organic Compounds; Soloshonok, V. A., Ed.; John Wiley & Sons: Chichester, 1999
53 Takeuchi, Y.; Konishi, M.; Hori, H.; Takehashi, T.; Kometani, T.; Kirk, K. L. Chem. Commun. 1998, 365-366
54 Takeuchi, Y.; Konishi, M.; Hori, H.; Takehashi, T.; Kometani, T.; Kirk, K. L. Enantiomer 1999, 4, 339
55 Takeuchi, Y.; Fukushima, A.; Tanaka, Y.; Takeuchi, Y.; Kabuto, K.; Kabuto, C. Chem. Commun. 2000, 787-788
56 Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001-7009   DOI   ScienceOn
57 Nieschalk, J.; O'Hagan, D. Chem. Commun. 1995, 719
58 Berkowitz, D. B.; Bose, M. J. Fluorine Chem. 2001, 112, 13   DOI   ScienceOn
59 Blackburn, G. M. Chem. Ind. (London) 1981, 134
60 McKenna, C. E.; Shen, P. J. Org. Chem. 1981, 46, 4573   DOI
61 Nieschalk, J.; O'Hagan, D. Chem. Commun. 1995, 719
62 Jakeman, D. L.; Ivory, A. J.; Willamson, M. P.; Blackburn, G. M. J. Med. Chem. 1998, 41, 4493
63 Jakeman, D. L.; Ivory, A. J.; Willamson, M. P.; Blackburn, G. M. J. Med. Chem. 1998, 41, 4493
64 Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498   DOI   ScienceOn
65 Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4265- 4568
66 Cho, M. J.; Cho, M. G.; Huh, S. C.; Kim, S. M.; Lee, K.; Koh, K. O.; Mang, J. Y. Bull. Korean Chem. Soc. 2006, 27, 857- 861   DOI   ScienceOn
67 Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897-6899   DOI   ScienceOn
68 Kim, D. Y.; Huh, S. C. Bull. Korean Chem. Soc. 2004, 25, 347-348   DOI   ScienceOn
69 Kim, D. Y.; Kim, S. M.; Koh, K. O.; Mang, J. Y. Bull. Korean Chem. Soc. 2003, 24, 1425-1426   DOI   ScienceOn
70 Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933-8938   DOI   ScienceOn