1864
J. H. Lee, D. Y. Kim
SPECIAL TOPIC
O’Hagan, D. Angew. Chem. Int. Ed. 2008, 47, 1179.
(k) Smits, R.; Cadicamo, C. D.; Burger, K.; Koksch, B.
Chem. Soc. Rev. 2008, 37, 1727.
(10) Selected examples of Mannich-type reactions of enolates,
see: (a) Sikert, M.; Schneider, C. Angew. Chem. Int. Ed.
2008, 47, 3631. (b) Itoh, J.; Fuchibe, K.; Akiyama, T.
Synthesis 2008, 1319. (c) Kobayashi, S.; Yazaki, R.; Seki,
K.; Ueno, M. Tetrahedron 2007, 63, 8425. (d) Saruhashi,
K.; Kobayashi, S. J. Am. Chem. Soc. 2006, 128, 11232.
(e) Kobayashi, S.; Ueno, M.; Saito, S.; Mizuki, Y.; Ishitani,
H.; Yamashita, Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101,
5476. (f) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K.
Angew. Chem. Int. Ed. 2004, 43, 1566. (g) Wenzel, A. G.;
Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
(11) (a) Hamashima, Y.; Sasamoto, N.; Umebayashi, N.;
Sodeoka, M. Chem. Asian J. 2008, 3, 1443. (b) Chen, Z.;
Morimoto, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem.
Soc. 2008, 130, 2170. (c) Kobayashi, S.; Gustafsson, T.;
Shimizu, Y.; Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8,
4923. (d) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei,
H.; Umebayashi, N.; Sodeoka, M. Angew. Chem. Int. Ed.
2005, 44, 1525. (e) Kang, Y. K.; Kim, D. Y. J. Org. Chem.
2009, 74, 5734. (f) Kim, E. J.; Kang, Y. K.; Kim, D. Y. Bull.
Korean Chem. Soc. 2009, 30, 1437. (g) Lee, J. H.; Kim, D.
Y. Adv. Synth. Catal. 2009, 351, 1779.
(5) For recent selected examples of catalytic asymmetric
fluorinations of active methines, see: (a) Hintermann, L.;
Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359. (b) Kim,
D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. (c) Hamashima,
Y.; Yagi, K.; Takano, H.; Tamás, L.; Sodeoka, M. J. Am.
Chem. Soc. 2002, 124, 14530. (d) Ma, J.-A.; Cahard, D.
Tetrahedron: Asymmetry 2004, 15, 1007. (e) Shibata, N.;
Ishimaru, T.; Nagai, T.; Kohno, J.; Toru, T. Synlett 2004,
1703. (f) Bernardi, L.; Jørgensen, K. A. Chem. Commun.
2005, 1324. (g) Kim, S. M.; Kim, H. R.; Kim, D. Y. Org.
Lett. 2005, 7, 2309. (h) Kim, H. R.; Kim, D. Y. Tetrahedron
Lett. 2005, 46, 3115. (i) Ishimaru, T.; Shibata, N.;
Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M.
Angew. Chem. Int. Ed. 2008, 47, 4157. (j) Lee, N. R.; Kim,
S. M.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 829.
(6) For asymmetric Michael-type reactions of a-fluoro-
malonates, see: (a) Kim, D. Y.; Kim, S. M.; Koh, K. O.;
Mang, J. Y. Bull. Korean Chem. Soc. 2003, 24, 1425.
(b) 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. (c) Kwon, B. K.; Kim, S. M.; Kim, D. Y.
J. Fluorine Chem. 2009, 130, 759. (d) Companyo, X.;
Hejnova, M.; Kamlar, M.; Vesely, J.; Moyano, A.; Rios, R.
Tetrahedron Lett. 2009, 50, 5051.
(7) For asymmetric Michael-type reactions of a-fluoro-b-keto
esters, see: (a) Nakamura, M.; Hajra, A.; Endo, K.;
Nakamura, E. Angew. Chem. Int. Ed. 2005, 44, 7248.
(b) He, R.; Wang, X.; Hashimoto, T.; Maruoka, K. Angew.
Chem. Int. Ed. 2008, 47, 9466. (c) Mang, J. Y.; Kwon, D.
G.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 259. (d) Han,
X.; Luo, J.; Liu, C.; Lu, Y. Chem. Commun. 2009, 2044.
(e) Li, H.; Zhang, S.; Yu, C.; Song, X.; Wang, W. Chem.
Commun. 2009, 2136. (f) Oh, Y.; Kim, S. M.; Kim, D. Y.
Tetrahedron Lett. 2009, 50, 4674.
(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) Furukawa, T.; Shibata, N.; Mizuta, S.; Nakamura, S.;
Toru, T.; Shiro, M. Angew. Chem. Int. Ed. 2008, 47, 8051.
(d) Moon, H. W.; Cho, M. J.; Kim, D. Y. Tetrahedron Lett.
2009, 50, 4896. (e) 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.
(9) For selected recent reviews, see: (a) 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. (b) Ting, A.; Schaus, S. E.
Eur. J. Org. Chem. 2007, 5797. (c) Marques, M. M. B.
Angew. Chem. Int. Ed. 2006, 45, 348. (d) Cordova, A. Acc.
Chem. Res. 2004, 37, 102.
(12) (a) Puglisi, A.; Benaglia, M.; Annunziata, R.; Rossi, D.
Tetrahedron: Asymmetry 2008, 19, 2258. (b) Fini, F.;
Bernardi, L.; Herrera, R. P.; Pettersen, D.; Ricci, A.;
Sgarzani, V. Adv. Synth. Catal. 2006, 348, 2043.
(c) Yamaoka, Y.; Miyabe, H.; Yasui, Y.; Takemoto, Y.
Synthesis 2007, 2571. (d) Tillman, A. L.; Ye, J.; Dixon, D. J.
Chem. Commun. 2006, 1191.
(13) (a) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett.
2001, 42, 6299. (b) Kim, D. Y.; Huh, S. C. Tetrahedron
2001, 57, 8933. (c) Park, E. J.; Kim, M. H.; Kim, D. Y.
J. Org. Chem. 2004, 69, 6897. (d) Kang, Y. K.; Kim, D. Y.
Tetrahedron Lett. 2006, 47, 4265. (e) Kang, Y. K.; Cho, M.
J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135. (f) Cho, M.
J.; Kang, Y. K.; Lee, N. R.; Kim, D. Y. Bull. Korean Chem.
Soc. 2007, 28, 2191. (g) Kim, S. M.; Kang, Y. K.; Cho, M.
J.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2007,
28, 2435. (h) Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett
2008, 1821. (i) Mang, J. Y.; Kim, D. Y. Bull. Korean Chem.
Soc. 2008, 29, 2091. (j) Kang, Y. K.; Kim, D. Y. Bull.
Korean Chem. Soc. 2008, 29, 2093. (k) Kim, D. Y. Bull.
Korean Chem. Soc. 2008, 29, 2036. (l) Mang, J. Y.; Kwon,
D. G.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 249.
(14) (a) Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659.
(b) Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527.
(15) Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005,
4481.
(16) Thenappen, A.; Burton, D. J. J. Org. Chem. 1991, 56, 273.
Synthesis 2010, No. 11, 1860–1864 © Thieme Stuttgart · New York