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SPECIAL TOPIC
(4) Recent reviews of asymmetric fluorinations, see:
(a) Ibrahim, H.; Togni, A. Chem. Commun. 2004, 1147.
(b) Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004,
104, 1. (c) Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104,
6119. (d) Oestreich, M. Angew. Chem. Int. Ed. 2005, 44,
2324. (e) Pihko, P. M. Angew. Chem. Int. Ed. 2006, 45, 544.
(f) Prakash, G. K. S.; Beier, P. Angew. Chem. Int. Ed. 2006,
45, 2172. (g) Bobbio, C.; Gouverneur, V. Org. Biomol.
Chem. 2006, 4, 2065. (h) Shibata, N.; Ishimaru, T.;
Nakamura, S.; Toru, T. J. Fluorine Chem. 2007, 128, 469.
(i) Brunet, V. A.; O’Hagan, D. Angew. Chem. Int. Ed. 2008,
47, 1179. (j) Smits, R.; Cadicamo, C. D.; Burger, K.;
Koksch, B. Chem. Soc. Rev. 2008, 37, 1727.
Harding, J. P.; Holmen, A.; Kothare, M.; Lehmann, A.;
Mattsson, J. P.; Nilsson, K.; Sunden, G.; Swanson, M.;
von Unge, S.; Woo, A. M.; Wyle, M. J.; Zheng, X. J. Med.
Chem. 2008, 51, 4315.
(7) (a) Steiner, D. D.; Mase, N.; Barbas, C. F. III Angew. Chem.
Int. Ed. 2005, 44, 3706. (b) Enders, D.; Hüttl, M. R. M.
Synlett 2005, 991. (c) Marigo, M.; Fielenbach, D.;
Braunton, A.; Kjoersgaard, A.; Jørgensen, K. A. Angew.
Chem. Int. Ed. 2005, 44, 3703. (d) Beeson, T. D.;
MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 8826.
(8) (a) Fukuzumi, T.; Shibata, N.; Sugiura, M.; Yasui, H.;
Nakamura, S.; Toru, T. Angew. Chem. Int. Ed. 2006, 45,
4973. (b) Mizuta, S.; Shibata, N.; Goto, Y.; Furukawa, T.;
Nakamura, S.; Toru, T. J. Am. Chem. Soc. 2007, 129, 6394.
(c) Fukuzumi, T.; Shibata, N.; Mizuta, S.; Nakamura, S.;
Toru, T.; Shiro, M. Angew. Chem. Int. Ed. 2008, 47, 8051.
Non-asymmetric version of conjugate addition of FBSM to
a,b-unsaturated ketones, see: (d) Prakash, G. K. S.; Zhao,
X.; Chacko, S.; Wang, F.; Vaghoo, H.; Olah, G. A. Beilstein
J. Org. Chem. 2008, 4, 1. (e) Ni, C.; Zhang, L.; Hu, J.
J. Org. Chem. 2008, 73, 5699.
(5) For recent selected examples of catalytic asymmetric
fluorinations, see: (a) Arai, S.; Oku, M.; Ishida, T.; Shioiri,
T. Tetrahedron Lett. 1999, 40, 6785. (b) Piana, S.;
Devillers, I.; Togni, A.; Rothlisberger, U. Angew. Chem. Int.
Ed. 2002, 41, 979. (c) Hamashima, Y.; Yagi, K.; Takano,
H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124,
14530. (d) Hamashima, Y.; Suzuki, T.; Takano, H.;
Shimura, Y.; Sodeoka, M. J. Am. Chem. Soc. 2005, 127,
10164. (e) Shibata, N.; Kohno, J.; Takai, K.; Ishimaru, T.;
Nakamura, S.; Toru, T.; Kanemasa, S. Angew. Chem. Int.
Ed. 2005, 44, 4204. (f) Nakamura, M.; Hajra, A.; Endo, K.;
Nakamura, E. Angew. Chem. Int. Ed. 2005, 44, 7248.
(g) Roelfes, G.; Boersma, A. J.; Feringa, B. L. Chem.
Commun. 2006, 635. (h) Burger, E. C.; Barron, B. R.;
Tunge, J. A. Synlett 2007, 2824. (i) Nie, J.; Zhu, H.-W.; Cui,
H.-F.; Hua, M.-Q.; Ma, J.-A. Org. Lett. 2007, 9, 3053.
(j) Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.;
Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem. Int. Ed.
2008, 47, 4157.
(9) (a) Li, Y.; Ni, C.; Liu, J.; Zhang, L.; Zheng, J.; Zhu, L.; Hu,
J. Org. Lett. 2006, 8, 1693. (b) Ni, C.; Li, Y.; Hu, J. J. Org.
Chem. 2006, 71, 6829.
(10) Prakash, G. K. S.; Chacko, S.; Alconcel, S.; Stewart, T.;
Mathew, T.; Olah, G. A. Angew. Chem. Int. Ed. 2007, 46,
4933.
(11) For selected examples of asymmetric conjugate additions of
malonates, see: (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K.
N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
(b) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc.
2001, 123, 4370. (c) Halland, N.; Aburel, P. S.; Jørgensen,
K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (d) Li, H.;
Wang, Y.; Tang, T.; Deng, L. J. Am. Chem. Soc. 2004, 126,
9906. (e) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.;
Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
(f) McCooey, S. H.; Connon, S. J. Angew. Chem. Int. Ed.
2005, 44, 6367. (g) Ye, J.; Dixon, D. J.; Hynes, P. S. Chem.
Commun. 2005, 4481. (h) Knudsen, K. R.; Mitchell, C. E.
T.; Ley, S. V. Chem. Commun. 2006, 66.
(12) (a) Christoffers, J.; Mann, A. Angew. Chem. Int. Ed. 2001,
40, 4591. (b) Denissova, I.; Barriault, L. Tetrahedron 2003,
59, 10105. (c) Christoffers, J.; Baro, A. Adv. Synth. Catal.
2005, 347, 1473. (d) Riant, O.; Hannedouche, J. Org.
Biomol. Chem. 2007, 5, 873. (e) Cozzi, P. G.; Hilgraf, R.;
Zimmermann, N. Eur. J. Org. Chem. 2007, 5969.
(13) Brandes, S.; Niess, B.; Bella, M.; Prieto, A.; Overgaard, J.;
Jørgensen, K. A. Chem. Eur. J. 2006, 12, 6039.
(6) For selected examples, see: (a) Kun, E.; Dummel, R. J.
Methods Enzymol. 1969, 13, 623. (b) Kollonitsch, J.;
Perkins, L. M.; Patchett, A. A.; Doldouras, G. A.; Marburg,
S.; Duggan, D. E.; Maycock, A. L.; Aster, S. D. Nature
1978, 274, 906. (c) Bey, P.; Gerhart, F.; Dorsselaer, V. V.;
Danzin, C. J. Med. Chem. 1983, 26, 1551. (d) Welch, J. T.
Tetrahedron 1987, 43, 3123. (e) Silverman, R. B.;Nanavati,
S. M. J. Med. Chem. 1990, 33, 931. (f) Grunewald, G. L.;
Caldwell, T. M.; Li, Q.; Slavica, M.; Criscione, K. R.;
Borchardt, R. T.; Wang, W. J. Med. Chem. 1999, 42, 3588.
(g) Gerus, I. I.; Kolomeitsev, A. A.; Kolycheva, M. I.;
Kukhar, V. P. J. Fluorine Chem. 2000, 105, 31. (h) Silhar,
P.; Pohl, R.; Votruba, I.; Hocek, M. Org. Biomol. Chem.
2005, 3, 3001. (i) Kudzma, L. V.; Huang, C. G.; Lessor, R.
A.; Rozov, L. A.; Afrin, S.; Kallashi, F.; McCutcheon, C.;
Ramig, D. J. Fluorine Chem. 2001, 111, 11. (j) Grunewald,
G. L.; Seim, M. R.; Regier, R. C.; Martin, J. L.; Gee, L.;
Drinkwater, N.; Criscione, K. R. J. Med. Chem. 2006, 49,
5424. (k) Parent, E. E.; Carlson, K. E.; Katzenellenbogen, J.
A. J. Org. Chem. 2007, 72, 5546. (l) Simeon, F. G.; Brown,
A. K.; Zoghbi, S. S.; Patterson, V. M.; Innis, R. B.; Pike, V.
W. J. Med. Chem. 2007, 50, 3256. (m) Alstermark, C.;
Amin, K.; Dinn, S.; Elebring, R. T.; Fjellstrom, O.;
Fitzpatrick, K.; Geiss, W. B.; Gottfries, J.; Guzzo, P. R.;
(14) Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.;
Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem. Int. Ed.
2008, 47, 4157.
(15) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545.
(16) CCDC-716267 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
Synthesis 2009, No. 9, 1525–1530 © Thieme Stuttgart · New York