Enantiopure trifluoromethylated β3,3-amino acids: Synthesis by asymmetric reformatsky reaction with stable analogues of trifluoromethyl N-tert-butanesulfinylketoimines and incorporation into α/β-peptides

Journal of Organic Chemistry

Volumn 78, Issue 3, 2013, Pages 1127-1137

  Grellepois, Fabienne ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; DIASTEREOSELECTIVITIES; ENANTIOPURE; REFORMATSKY REACTION; REFORMATSKY REAGENTS; TRI-PEPTIDES; TRIFLUOROMETHYL;

AMINO ACIDS;

SYNTHESIS (CHEMICAL);

AMINO ACID DERIVATIVE; KETONE DERIVATIVE; TRIPEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL REACTION; REFORMATSKY REACTION; ROOM TEMPERATURE; SYNTHESIS;

AMINO ACIDS; BUTANES; ESTERS; IMINES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PEPTIDES; STEREOISOMERISM; SULFONAMIDES;

EID: 84873356888     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302549v     Document Type: Article

References (86)

1. Von Nussbaum, F. and Spiteller, P. In Highlights in Bioorganic Chemistry: Methods and Applications; Schmuck, C. and Wennemers, H., Eds.; Wiley-VCH: Weinheim, 2004; pp 63-89.
2. Sleebs, B. E.; Van Nguyen, T. T.; Hughes, A. B. Org. Prep. Proced. Int. 2009, 41, 429-478
3. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015-2022
4. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180
5. Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232
6. Martinek, T. A.; Fülöp, F. Eur. J. Biochem. 2003, 270, 3657-3666
7. Seebach, D.; Hook, D. F.; Glättli, A. Biopolymers (Peptide Sci.) 2006, 84, 23-37
8. Fülöp, F.; Martikek, T. A.; Tóth, G. K. Chem. Soc. Rev. 2006, 35, 323-334
9. Godballe, T.; Nilsson, L. L.; Petersen, P. D.; Jenssen, H. Chem. Biol. Drug Des. 2011, 41, 107-116
10. Vasudev, P. G.; Chatterjee, S.; Narayanaswamy, S.; Padmanabhan, B. Chem. Rev. 2011, 111, 657-687
11. Horne, W. S.; Gellman, S. H. Acc. Chem. Res. 2008, 41, 1399-1408
12. Ludwig, K. A.; Pilsl, L. K. A.; Reiser, O. Amino Acids 2011, 41, 709-718
13. Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991-8035
14. Ma, J. A. Angew. Chem., Int. Ed. 2003, 42, 4290-4299
15. Bandala, Y.; Juaristi, E. In Amino Acids, Peptides and Proteines in Organic Chemistry. Vol. 1: Origins and Synthesis of Amino Acids; Hughes, A. B., Ed.; Wiley-VCH: Weinheim, 2009; pp 291-365.
16. Weiner, B.; Szymański, W.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L. Chem. Soc. Rev. 2010, 39, 1656-1691
17. Rudat, J.; Brucher, B. R.; Syldatk, C. AMB Express 2012, 2, 11
18. Böhm, H. J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637-640
19. Uneyama, K. In Organofluorine Chemistry; Blackwell Publishing Ltd.: Oxford, 2006.
20. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
21. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319
22. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
23. Bégué, J. P.; Bonnet-Delpon, D. In Bioorganic and Medicinal Chemistry of Fluorine; Wiley-VCH: Weinheim, 2008.
24. Hunter, L. Beilstein J. Org. Chem. 2010, 6, No. 38.
25. Salwiczek, M.; Nyakatura, E. K.; Gerling, U. I. M.; Ye, S.; Koksch, B. Chem. Soc. Rev. 2012, 41, 2135-2171
26. Qiu, X. L.; Meng, W. D.; Qing, F. L. Tetrahedron 2004, 60, 6711-6745
27. Qiu, X. L.; Qing, F. L. Eur. J. Org. Chem. 2011, 3261-3278
28. Mikami, K.; Fustero, S.; Sánchez-Rosello, M.; Aceňa, J. L.; Soloshonok, V.; Sorochinsky, A. Synthesis 2011, 3045-3079
29. For an introduction of this denomination, see: Hintermann, T.; Seebach, D. Synlett 1997, 437-438
30. Soloshonok, V. A.; Kirilenko, A. C.; Galushko, S. V.; Kukhar, V. P. Tetrahedron Lett. 1994, 35, 5063-5064
31. Fustero, S.; Salavert, E.; Pina, B.; Ramirez de Arellano, C.; Asensio, A. Tetrahedron 2001, 57, 6475-6486
32. Lebouvier, N.; Laroche, C.; Huguenot, F.; Brigaud, T. Tetrahedron Lett. 2002, 43, 2827-2830
33. Funabiki, K.; Nagamori, M.; Matsui, M. J. Fluorine Chem. 2004, 125, 1347-1350
34. Huguenot, F.; Brigaud, T. J. Org. Chem. 2006, 71, 2159-2162
35. Michaut, V.; Metz, F.; Paris, J. M.; Plaquevent, J. C. J. Fluorine Chem. 2007, 128, 889-895
36. Dos Santos, M.; Crousse, B.; Bonnet-Delpon, D. Synlett 2008, 399-401
37. Ishida, Y.; Iwahashi, N.; Nishizono, N.; Saigo, K. Tetrahedron Lett. 2009, 50, 1889-1892
38. Fustero, S.; del Pozo, C.; Catalán, S.; Alemán, J.; Parra, A.; Marcos, V.; Garcia Ruano, J. L. Org. Lett. 2009, 11, 641-644
39. Mimura, H.; Kawada, K.; Yamashita, T.; Sakamoto, T.; Kikugawa, Y. J. Fluorine Chem. 2010, 131, 477-486
40. Shibata, N.; Nishimine, T.; Shibata, N.; Tokunaga, E.; Kawada, K.; Kagawa, T.; Sorochinsky, A. E.; Soloshonok, V. A. Chem. Commun. 2012, 48, 4124-4126
41. Soloshonok, V. A.; Svedas, V. K.; Kukhar, V. P.; Kirilenko, A. G.; Rybakova, A. V.; Solodenko, V. A.; Fokina, N. A.; Kogut, O. V.; Galaev, I.Yu.; Kozlova, E. V.; Shishkina, I. P.; Galushko, S. V. Synlett 1993, 5, 339-341
42. Soloshonok, V. A.; Kirilenko, A. C.; Fokina, N. A.; Shishkina, I. P.; Galushko, S. V.; Kukhar, V. P.; Svedas, V. K.; Kozlova, E. V. Tetrahedron Asymmetry 1994, 5, 1119-1126
43. Soloshonok, V. A.; Kukhar, V. P. Tetrahedron 1996, 52, 6953-6964
44. Soloshonok, V. A.; Ono, T.; Soloshonok, I. V. J. Org. Chem. 1997, 62, 7538-7539
45. Dai, Q.; Yang, W.; Zhang, X. Org. Lett. 2005, 7, 5343-5345
46. Soloshonok, V. A.; Ohkura, H.; Yasumoto, M. J. Fluorine Chem. 2006, 127, 924-929
47. Soloshonok, V. A.; Ohkura, H.; Yasumoto, M. J. Fluorine Chem. 2006, 127, 930-935
48. Michaut, V.; Metz, F.; Paris, J. M.; Plaquevent, J. C. J. Fluorine Chem. 2007, 128, 500-506
49. Weiß, M.; Gröger, H. Synlett 2009, 1251-1254
50. Volonterio, A.; Bellosta, S.; Bravo, S.; Canavesi, M.; Corradi, E.; Meille, S. V.; Monetti, M.; Moussier, N.; Zanda, M. Eur. J. Org. Chem. 2002, 428-438
51. Volonterio, A.; Bellosta, S.; Bravin, F.; Belluci, M. C.; Bruché, L.; Colombo, G.; Malpezzi, L.; Mazzini, S.; Meille, S. V.; Meli, M.; Ramirez de Arellano, C.; Zanda, M. Chem.-Eur. J. 2003, 9, 4510-4522
52. Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1-15
53. Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913-9914
54. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995
55. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600-3740
56. Tang, T.; Ellman, J. A. J. Org. Chem. 1999, 64, 12-13
57. Tang, T.; Ellman, J. A. J. Org. Chem. 2002, 67, 7819-7832
58. Zhao, C. H.; Liu, L.; Wang, D.; Chen, Y. J. Eur. J. Org. Chem. 2006, 2977-2986
59. Morriello, G. J.; Mills, S. G.; Johnson, T.; Reibarkh, M.; Chicchi, G.; DeMartino, J.; Kurtz, M.; Davies, P.; Tsao, K. L. C.; Zheng, S.; Tong, X.; Carlson, E.; Townson, K.; Tattersall, F. D.; Wheeldon, A.; Boyce, S.; Collinson, N.; Rupniak, N.; Moore, S.; DeVita, R. J. Bioorg. Med. Chem. Lett. 2010, 20, 2007-2012
60. Kirchberg, S.; Tani, S.; Ueda, K.; Yamaguchi, J.; Studer, A.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 2387-2391
61. Kamau, M. G.; Harikrishnan, L. S.; Finlay, H. J.; Qiao, J. X.; Jiang, J.; Poss, M. A.; Salvati, M. E.; Wexler, R. R.; Lawrence, R. M. Tetrahedron 2012, 68, 2696-2703
62. Brinner, K.; Doughan, B.; Poon, D. J. Synlett 2009, 991-993
63. Wang, H.; Zhao, X.; Li, Y.; Lu, L. Org. Lett. 2006, 8, 1379-1381
64. Liu, Z. J.; Liu, J. T. Chem. Commun. 2008, 5233-5235
65. Xiao, H.; Huang, Y.; Qing, F. L. Tetrahedron: Asymmetry 2010, 21, 2949-2955
66. Zhang, F.; Liu, Z. J.; Liu, J. T. Org. Biomol. Chem. 2011, 9, 3625-3628
67. Liu, Y. L.; Huang, Y.; Qing, F. L. Tetrahedron 2012, 68, 4955-4961
68. Kuduk, S. C.; Di Marco, C. N.; Pitzenberger, S. M.; Tsou, N. Tetrahedron Lett. 2006, 47, 2377-2381
69. Fustero, S.; Cuňat, A. C.; Flores, S.; Báez, C.; Oliver, J.; Cynamon, M.; Gütschow, M.; Mertens, M. D.; Delgado, O.; Tresardern, G.; Trabanco, A. A. Chem.-Eur. J. 2011, 17, 14772-14784
70. Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382
71. Lauzon, C.; Charette, A. B. Org. Lett. 2006, 8, 2743-2745
72. Ocampo, R.; Dolbier, W. R. Tetrahedron 2004, 60, 9325-9374
73. Pace, V.; Hoyos, P.; Castoldi, L.; Dominguez de Maria, P.; Alcantras, A. R. ChemSusChem 2012, 5, 1369-1372
74. Zanda, M. New J. Chem. 2004, 28, 1401-1411
75. Han, S. Y.; Kim, Y. A. Tetrahedron 2004, 60, 2447-2467
76. Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005, 61, 10827-10852
77. Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606-631
78. Joullié, M. M.; Lassen, K. M. ARKIVOC 2010, viii, 189-250
79. Dal Pozzo, A.; Bergonzi, R.; Ni, M. Tetrahedron Lett. 2001, 42, 3925-3927
80. Dal Pozzo, A.; Ni, M.; Muzi, L.; Caporale, A.; deCastiglione, R.; Kaptein, B.; Broxterman, Q. B.; Formaggio, F. J. Org. Chem. 2002, 67, 6372-6375
81. Dal Pozzo, A.; Ni, M.; Muzi, L.; deCastiglione, R.; Mondelli, R.; Mazzini, S.; Penco, S.; Pisano, C.; Castorina, M.; Giannini, G. J. Med. Chem. 2006, 49, 1808-1817
82. Chaume, G.; Lensen, N.; Caupène, C.; Brigaud, T. Eur. J. Org. Chem. 2009, 5717-5724
83. Koksch, B.; Quaedflieg, P. J. L. M.; Michel, T.; Burger, K.; Broxterman, Q. B.; Schoemaker, H. E. Tetrahedron Asymmetry 2004, 15, 1401-1407
84. Sureshbabu, V. V.; Hemantha, H. P. Arkivoc 2008, ii, 243-249
85. Carpino, L. A.; Beyermann, M.; Wenschuh, H.; Bienert, M. Acc. Chem. Res. 1996, 29, 268-274
86. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3 rd ed.; Pergamon Press: Oxford, 1988; p 360.