Communication
Organic & Biomolecular Chemistry
addition with a variety of isatin derivatives. The fluorous
ligand can be easily recovered and reused at least 3 times
without significant loss in its activity.
hedron Lett., 2001, 42, 9015; (h) H. B. Rasmussen and
J. K. Macleod, J. Nat. Prod., 1997, 60, 1152; (i) T. Kawasaki,
M. Nagaoka, T. Satoh, A. Okamoto, R. Ukon and A. Ogawa,
Tetrahedron, 2004, 60, 3493; ( j) K. Toshinori, S. Shizuka,
S. Hideyuki, O. Ayumi, I. Haruaki, K. Takaaki and
K. Juńichi, J. Nat. Prod., 2006, 69, 1517; (k) T. Tokunaga,
W. E. Hume, T. Umezome, K. Okazaki, Y. Ueki,
K. Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji,
H. Noguchi and R. Nagata, J. Med. Chem., 2001, 44, 4641;
(l) T. Tokunaga, W. E. Hume, J. Nagamine, T. Kawamura,
M. Taiji and R. Nagata, Bioorg. Med. Chem. Lett., 2005, 15,
1789.
Acknowledgements
We are grateful for financial support from the Jiangsu National
Science Foundation of China (BK 20131346).
Notes and references
10 Q. Guo, M. Bhanushali and C. G. Zhao, Angew. Chem., Int.
Ed., 2010, 49, 9460.
1 D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul,
J. Am. Chem. Soc., 1991, 113, 726.
11 G. Luppi, P. G. Cozzi, M. Monari, B. Kaptein,
Q. B. Broxterman and C. Tomasini, J. Org. Chem., 2005, 70,
7418.
12 F. Braude and H. G. Lindwall, J. Am. Chem. Soc., 1933, 55,
325.
13 S. E. Denmark and J. Fu, Chem. Rev., 2003, 103, 2763.
14 J. A. Marshall, Chem. Rev., 2000, 100, 3163.
15 R. Shintani, M. Inoue and T. Hayashi, Angew. Chem., Int.
Ed., 2006, 45, 3353.
2 E. J. Corey, N. Imai and H. Y. Zhang, J. Am. Chem. Soc.,
1991, 113, 728.
3 H. A. McManusn and P. J. Guiry, Chem. Rev., 2004, 104,
4151.
4 (a) J. R. Gao, H. Wu, B. Xiang, W. B. Yu, L. Han and
Y. X. Jia, J. Am. Chem. Soc., 2013, 135, 2983; (b) J. George
and B. V. S. Reddy, Org. Biomol. Chem., 2012, 10, 4731.
5 J. George and B. V. S. Reddy, Adv. Synth. Catal., 2013, 355,
383.
16 L. Liu, S. Zhang, F. Xue, G. Lou, H. Zhang, S. Ma, W. Duan
and W. Wang, Chem. – Eur. J., 2011, 17, 7791.
6 T. Risgaard, K. V. Gothelf and K. A. Jørgensen, Org. Biomol.
Chem., 2003, 1, 153–156.
17 (a) T. Ishimaru, N. Shibata, J. Nagai, S. Nakamura, T. Toru
and S. Kanemasa, J. Am. Chem. Soc., 2006, 128, 16488;
(b) D. Sano, K. Nagata and T. Itoh, Org. Lett., 2008, 10,
1593.
18 Q. Ren, J. Y. Huang, L. Wang, W. J. Li, H. Liu, X. F. Jiang
and J. Wang, ACS Catal., 2012, 2, 2622.
19 B. E. Maryanoff and A. B. Reitz, Chem. Rev., 1989, 89, 863.
20 (a) D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free,
W. L. Rogers, S. A. Smith, J. M. DeForrest, R. S. Oehl and
E. W. Petrillo, J. Med. Chem., 1995, 38, 4557.
21 (a) B. Stowasser, K. H. Budt, J. Q. Li, A. Peyman and
D. Ruppert, Tetrahedron Lett., 1992, 33, 6625; (b) For a
review about the biological activity of amino phosphonic
acids, see: P. Kafarski and B. Lejczak, Phosphorus, Sulfur
Silicon Relat. Elem., 1991, 63, 193.
22 (a) P. A. Gurevich, G. Z. Akhmetova, A. T. Gubaidullin,
V. V. Moskva and I. N. A. Litvinov, Russ. J. Gen. Chem.,
1998, 68, 1501; (b) J. Shankar, K. Karnakar, B. Srinivas and
Y. V. D. Nageswar, Tetrahedron Lett., 2010, 51, 3938;
(c) L. Peng, I. L. Wang, J. F. Bai, L. N. Jia, Q. C. Yang,
Q. C. Huang, X. Y. Xu and L. X. Wang, Tetrahedron Lett.,
2011, 52, 1157.
7 K. Lang, J. Park and S. Hong, J. Org. Chem., 2010, 75, 6424.
8 (a) Y. Kamano, H. P. Zhang, Y. Kchihara, H. Kizu,
K. Komiyama and G. R. Pettit, Tetrahedron Lett., 1995, 36,
2783; (b) J. Kohno, Y. Koguchi, M. Nishio, K. Nakao,
M. Kuroda, R. Shimizu, T. Ohnuki and S. Komatsubara,
J. Org. Chem., 2000, 65, 990; (c) Y. Q. Tang, I. Sattler,
R. Thiericke, S. Grabley and X. Z. Feng, Eur. J. Org. Chem.,
2001, 261; (d) C. Y. Gan and T. Kam, Tetrahedron Lett.,
2009, 50, 1059.
9 (a) C. V. Galliford and K. A. Scheidt, Angew. Chem., Int. Ed.,
2007, 46, 8748; (b) J. Kohno, Y. Koguchi, M. Nishio,
K. Nakao, M. Juroda, R. Shimizu, T. Ohnuki and
S. Komatsubara, J. Org. Chem., 2000, 65, 990; (c) K. A. Brian
and M. W. Robert, Org. Lett., 2003, 5, 197; (d) N. Basse,
S. Piguel, D. Papapostolou, A. Ferrier-Berthelot, N. Richy,
M. Pagano, P. Sarthou, J. Sobczak-Thépot, M. Reboud-
Ravaux and J. Vidal, J. Med. Chem., 2007, 50, 2842;
(e) K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter,
G. M. L. Patterson, S. Shaffer, C. D. Smith and T. A. Smitka,
J. Am. Chem. Soc., 1994, 116, 9935; (f) J. L. Jimenez,
U. Huber, R. E. Moore and G. M. L. Patterson, J. Nat. Prod.,
1999, 62, 569; (g) A. Fréchard, N. Fabre, C. Péan,
S. Montaut, M. T. Fauvel, P. Rollin and I. Fourasté, Tetra-
23 T. Deng and C. Cai, J. Fluorine Chem., 2013, 156, 183.
5846 | Org. Biomol. Chem., 2014, 12, 5843–5846
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