Recent Developments in the Synthesis of Fluorine-Containing β-Amino Acids and β-Lactams

doi:10.6023/cjoc201303020

Abstract

Fluorine-containing β-amino acids and β-lactams have attracted appreciable attention due to their wide application in organic chemistry, drug discovery, and protein biology. Accordingly, the development of efficient synthetic methods is of considerable interest in academia and industry. The synthesis and resolution are achieved. This review briefly summarizes the recent development in the methodologies for the synthesis of fluorine-containing β-amino acids and β-lactams with classification by the species of the fluorine-containing β-amino acids (α-fluorinated β-amino acids, α-trifluoromethyl β-amino acids, and β-trifluoromethyl β-amino acids).

Key words: fluorine-containing β-amino acid, fluorine-containing β-lactam, synthesis

Cite this article

Lin Daizong, Wang Jiang, Liu Hong. Recent Developments in the Synthesis of Fluorine-Containing β-Amino Acids and β-Lactams[J]. Chin. J. Org. Chem., 2013, 33(10): 2098-2107.

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References

[1] Wang, J.; Liu, H. Chin. J. Org. Chem. 2011, 31, 1785.
[2] Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[3] Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
[4] Sutherland, A.; Willis, C. L. Nat. Prod. Rep. 2000, 17, 621.
[5] Qiu, X. L.; Meng, W. D.; Qing, F. L. Tetrahedron 2004, 60, 6711.
[6] Qiu, X. L.; Qing, F. L. Eur. J. Org. Chem. 2011, 3261.
[7] March, T. L.; Johnston, M. R.; Duggan, P. J.; Gardiner, J. Chem. Biodiversity 2012, 9, 2410.
[8] Clader, J. W. J. Med. Chem. 2004, 47, 1.
[9] Rosenblum, S. B.; Huynh, T.; Afonso, A.; Davis, H. R.; Yumibe, N.; Clader, J. W.; Burnett, D. A. J. Med. Chem. 1998, 41, 973.
[10] Nakayama, K.; Kawato, H. C.; Inagaki, H.; Nakajima, R.; Kitamura, A.; Someya, K.; Ohta, T. Org. Lett. 2000, 2, 977.
[11] Kawato, H. C.; Nakayama, K.; Inagaki, H.; Nakajima, R.; Kitamura, A.; Someya, K.; Ohta, T. Org. Lett. 2000, 2, 973.
[12] Thornberry, N. A.; Weber, A. E. Curr. Top. Med. Chem. 2007, 7, 557.
[13] Biftu, T.; Feng, D.; Qian, X. X.; Liang, G. B.; Kieczykowski, G.; Eiermann, G.; Huaibing, H. B.; Lelting, B.; Lyons, K.; Petrov, A.; Sinha-Roy, R.; Zhang, B.; Scapin, G.; Patel, S.; Gao, Y. D.; Singh, S.; Wu, J.; Zhang, X. P.; Thornberry, N. A.; Weber, A. E. Bioorg. Med. Chem. Lett. 2007, 17, 49.
[14] Ojima, I.; Lin, S. N.; Slater, J. C.; Wang, T.; Pera, P.; Bernacki, R. J.; Ferlini, C.; Scambia, G. Bioorg. Med. Chem. 2000, 8, 1619.
[15] Pan, Y. H.; Zhao, Y. J.; Ma, T.; Yang, Y. Y.; Liu, H. J.; Jiang, Z. Y.; Tan, C. H. Chem.-Eur. J. 2010, 16, 779.
[16] Andrews, P. C.; Bhaskar, V.; Bromfield, K. M.; Dodd, A. M.; Duggan, P. J.; Duggan, S. A. M.; McCarthy, T. D. Synlett 2004, 791.
[17] Duggan, P. J.; Johnston, M.; March, T. L. J. Org. Chem. 2010, 75, 7365.
[18] Hook, D. F.; Gessier, F.; Noti, C.; Kast, P.; Seebach, D. ChemBioChem 2004, 5, 691.
[19] Davis, F. A.; Reddy, R. E. Tetrahedron: Asymmetry 1994, 5, 955.
[20] Peddie, V.; Pietsch, M.; Bromfield, K. M.; Pike, R. N.; Duggan, P. J.; Abell, A. D. Synthesis-Stuttgart 2010, 1845.
[21] Ohba, T.; Ikeda, E.; Takei, H. Bioorg. Med. Chem. Lett. 1996, 6, 1875.
[22] Gessier, F.; Noti, C.; Rueping, M.; Seebach, D. Helv. Chim. Acta 2003, 86, 1862.
[23] Yoshinari, T.; Gessier, F.; Noti, C.; Beck, A. K.; Seebach, D. Helv. Chim. Acta 2011, 94, 1908.
[24] Thaisrivongs, S.; Schostarez, H. J.; Pals, D. T.; Turner, S. R. J. Med. Chem. 1987, 30, 1837.
[25] Uoto, K.; Ohsuki, S.; Takenoshita, H.; Ishiyama, T.; Iimura, S.; Hirota, Y.; Mitsui, I.; Terasawa, H.; Soga, T. Chem. Pharm. Bull. 1997, 45, 1793.
[26] Fokina, N. A.; Kornilov, A. M.; Kukhar, V. P. J. Fluorine Chem. 2001, 111, 69.
[27] Soloshonok, V. A.; Ohkura, H.; Sorochinsky, A.; Voloshin, N.; Markovsky, A.; Belik, M.; Yamazaki, T. Tetrahedron Lett. 2002, 43, 5445.
[28] Sorochinsky, A.; Voloshin, N.; Markovsky, A.; Belik, M.; Yasuda, N.; Uekusa, H.; Ono, T.; Berbasov, D. O.; Soloshonok, V. A. J. Org. Chem. 2003, 68, 7448.
[29] Staas, D. D.; Savage, K. L.; Homnick, C. F.; Tsou, N. N.; Ball, R. G. J. Org. Chem. 2002, 67, 8276.
[30] Honda, T.; Wakabayashi, H.; Kanai, K. Chem. Pharm. Bull. 2002, 50, 307.
[31] Otaka, A.; Watanabe, J.; Yukimasa, A.; Sasaki, Y.; Watanabe, H.; Kinoshita, T.; Oishi, S.; Tamamura, H.; Fujii, N. J. Org. Chem. 2004, 69, 1634.
[32] Niida, A.; Tomita, K.; Mizumoto, M.; Tanigaki, H.; Terada, T.; Oishi, S.; Otaka, A.; Inui, K.; Fujii, N. Org. Lett. 2006, 8, 613.
[33] Boyer, N.; Gloanec, P.; De Nanteuil, G.; Jubault, P.; Quirion, J. C. Eur. J. Org. Chem. 2008, 4277.
[34] Boyer, N.; Gloanec, P.; De Nanteuil, G.; Jubault, P.; Quirion, J. C. Tetrahedron 2007, 63, 12352.
[35] Sato, K.; Tarui, A.; Matsuda, S.; Omote, M.; Ando, A.; Kumadaki, I. Tetrahedron Lett. 2005, 46, 7679.
[36] Tarui, A.; Ozaki, D.; Nakajima, N.; Yokota, Y.; Sokeirik, Y. S.; Sato, K.; Orriote, M.; Kumadaki, I.; Ando, A. Tetrahedron Lett. 2008, 49, 3839.
[37] Avenoza, A.; Busto, J. H.; Jimenez-Oses, G.; Peregrina, J. M. J. Org. Chem. 2005, 70, 5721.
[38] Pang, W.; Zhu, S. F.; Jiang, H. F.; Zhu, S. Z. Tetrahedron 2006, 62, 11760.
[39] Fustero, S.; Chiva, G.; Piera, J.; Sanz-Cervera, J. F.; Volonterio, A.; Zanda, M.; de Arellano, C. R. J. Org. Chem. 2009, 74, 3122.
[40] Shimada, T.; Yoshioka, M.; Konno, T.; Ishihara, T. Chem. Commun. 2006, 3628.
[41] Jakowiecki, J.; Loska, R.; Makosza, M. J. Org. Chem. 2008, 73, 5436.
[42] Mohar, B.; Stephan, M.; Urleb, U. Tetrahedron 2010, 66, 4144.
[43] Lin, D. Z.; Lv, L.; Wang, J.; Ding, X.; Jiang, H. L.; Liu, H. J. Org. Chem. 2011, 76, 6649.
[44] Jiang, J. L.; Shah, H.; DeVita, R. J. Org. Lett. 2003, 5, 4101.
[45] Michaut, V.; Metz, F.; Paris, J. M.; Plaquevent, J. C. J. Fluorine Chem. 2007, 128, 889.
[46] Ishida, Y.; Iwahashi, N.; Nishizono, N.; Saigo, K. Tetrahedron Lett. 2009, 50, 1889.
[47] Soloshonok, V. A.; Ono, T. J. Org. Chem. 1997, 62, 3030.
[48] Ono, T.; Kukhar, V. P.; Soloshonok, V. A. J. Org. Chem. 1996, 61, 6563.
[49] Soloshonok, V. A.; Ohkura, H.; Yasumoto, M. J. Fluorine Chem. 2006, 127, 924.
[50] Soloshonok, V. A.; Ohkura, H.; Yasumoto, M. J. Fluorine Chem. 2006, 127, 930.
[51] Begue, J. P.; Bonnet-Delpon, D.; Crousse, B.; Legros, J. Chem. Soc. Rev. 2005, 34, 562.
[52] Huguenot, F.; Brigaud, T. J. Org. Chem. 2006, 71, 2159.
[53] Dos Santos, M.; Crousse, B.; Bonnet-Delpon, D. Synlett 2008, 399.
[54] Fustero, S.; Jimenez, D.; Sanz-Cervera, J. F.; Sanchez-Rosello, M.; Esteban, E.; Simon-Fuentes, A. Org. Lett. 2005, 7, 3433.
[55] Sergeeva, N. N.; Golubev, A. S.; Hennig, L.; Findeisen, M.; Paetzold, E.; Oehme, G.; Burger, K. J Fluorine Chem 2001, 111, 41.
[56] Sergeeva, N. N.; Golubev, A. S.; Burger, K. Synthesis-Stuttgart 2001, 281.
[57] Kuznetsova, L.; Ungureanu, I. M.; Pepe, A.; Zanardi, I.; Wu, X. Y.; Ojima, I. J. Fluorine Chem. 2004, 125, 487.
[58] Jiang, Z. X.; Qing, F. L. J. Org. Chem. 2004, 69, 5486.
[59] Rinaudo, G.; Narizuka, S.; Askari, N.; Crousse, B.; Bonnet-Delpon, D. Tetrahedron Lett. 2006, 47, 2065.
[60] Fustero, S.; del Pozo, C.; Catalan, S.; Aleman, J.; Parra, A.; Marcos, V.; Ruano, J. L. G. Org. Lett. 2009, 11, 641.
[61] Ruano, J. L. G.; Aleman, J.; Catalan, S.; Marcos, V.; Monteagudo, S.; Parra, A.; del Pozo, C.; Fustero, S. Angew. Chem., Int. Ed. 2008, 47, 7941.

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