N-alkylation of N-arylsulfonyl-α-amino acid methyl esters by trialkyloxonium tetrafluoroborates

Tetrahedron

Volumn 67, Issue 50, 2011, Pages 9708-9714

  De Marco, Rosaria ^a   Di Gioia, Maria Luisa ^a   Liguori, Angelo ^a   Perri, Francesca ^a   Siciliano, Carlo ^a   Spinella, Mariagiovanna ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Amino acids; N Alkylation; N Arylsulfonamides; Triethyloxonium tetrafluoroborate; Trimethyloxonium tetrafluoroborate

Indexed keywords

ESTER DERIVATIVE; N ARYLSULFONYL A AMINO ACID METHYL ESTER; N ETHYL N 4 CHLOROPHENYLSULFONYL L LEUCINE METHYL ESTER; N ETHYL N 4 FLUOROPHENYLSULFONYL L VALINE METHYL ESTER; N ETHYL N 4 METHOXYPHENYLSULFONYL ALANINE METHYL ESTER; N ETHYL N 4 METHYLPHENYLSULFONYL ALANINE METHYL ESTER; N METHYL N 4 CHLOROPHENYLSULFONYL ALANINE METHYL ESTER; N METHYL N 4 FLUOROPHENYLSULFONYL ALANINE METHYL ESTER; N METHYL N 4 METHOXYPHENYLSULFONYL ALANINE METHYL ESTER; N METHYL N 4 METHYLPHENYLSULFONYL ALANINE METHYL ESTER; N METHYL N 4 NITROPHENYLSULFONYL ALANINE METHYL ESTER; N METHYL N 4 NITROPHENYLSULFONYL ISOLEUCINE METHYL ESTER; N METHYL N 4 NITROPHENYLSULFONYL PHENYLALANINE METHYL ESTER; N METHYL N 4 NITROPHENYLSULFONYL VALINE METHYL ESTER; TRIALKYLOXONIUM TETRAFLUOROBORATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; PRIORITY JOURNAL;

EID: 80655136937     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.042     Document Type: Article

References (77)

1. C. Gilon, M.A. Dechantsreiter, F. Burkhart, A. Friedler, and H. Kessler M. Goodman, A. Felix, L. Moroder, C. Toniolo, Synthesis of Peptides and Peptidomimetics, Houben-Weyl Methods of Organic Chemistry Vol. E 22c 2003 Thieme Stuttgart, Germany 215 271
2. See for example: C.A. Bewley, and D.J. Faulkner Angew. Chem. 110 1998 2280 2297
3. Angew. Chem., Int. Ed. 37 1998 2162 2178
4. R.P. Cheng, S.H. Gellman, and W.F. DeGrado Chem. Rev. 101 2001 3219 3232
5. M.A. Schmitt, S.H. Choi, I.A. Guzei, and S.H. Gellman J. Am. Chem. Soc. 127 2005 13130 13131
6. S. Uhlig, L. Ivanova, D. Petersen, and R. Kristensen Toxicon 53 2009 734 742
7. M.G. Baxter, D. Gott, A.A. Miller, and I. Saunders J. Pharmacol. 59 1977 455 459
8. T. Hornbogen, M. Glinski, and R. Zocher Eur. J. Plant Pathol. 108 2002 713 718
9. K. Muthusamy, P.I. Arvidsson, P. Govender, H.G. Kruger, G.E.M. Maguire, and T. Govender Bioorg. Med. Chem. Lett. 20 2010 1360 1362
10. R.M. Wenger Helv. Chim. Acta 66 1983 2308 2321
11. R.M. Wenger Helv. Chim. Acta 66 1983 2672 2702
12. R.M. Wenger Helv. Chim. Acta 67 1984 502 525
13. P. Jouin, J. Poncet, M.-N. Dufour, A. Pantaloni, and B. Castro J. Org. Chem. 54 1989 617 627
14. G.R. Pettit, Y. Kamano, C.L. Herald, C. Dufresne, R.B. Bates, J.M. Schmidt, R.L. Cerny, and H. Kizu J. Org. Chem. 55 1990 2989 2990
15. G.R. Pettit, Y. Kamano, C.L. Herald, Y. Fujii, H. Kizu, M.R. Boyd, F.E. Boettner, D.L. Doubek, J.M. Schmidt, J.-C. Chapuis, and C. Michael Tetrahedron 49 1993 9151 9170
16. J.M. Ramanjulu, X. Ding, and M.M. Jouillié J. Org. Chem. 62 1997 4961 4969
17. K.A. Witt, T.J. Gillespie, J.D. Huber, R.D. Egleton, and T.P. Davis Peptides 22 2001 2329 2343
18. A.M. Bodles, O.M.A. El-Agnaf, B. Greer, D.J.S. Guthrie, and G. Brent Irvine Neuroscience 359 2004 89 93
19. For a complete review, see: L. Aurelio, R.T.C. Brownlee, and A.B. Hughes Chem. Rev. 104 2004 5823 5846 and references cited therein
20. D.W. Hansen, and D. Pilipauskas J. Org. Chem. 50 1985 945 950
21. J.R. Coggins, and N.L. Benoiton Can. J. Chem. 49 1971 1968 1971
22. J.R. McDermott, and N.L. Benoiton Can. J. Chem. 51 1973 1915 1919
23. S.T. Cheung, and N.L. Benoiton Can. J. Chem. 55 1977 906 910
24. F.M. Chen, and N.L. Benoiton Can. J. Chem. 55 1977 1433 1435
25. R. Friedinger, J.S. Hinkle, D.S. Perlow, and B.H. Arison J. Org. Chem. 48 1983 77 81
26. Y. Ohfune, N. Kurokawa, N. Higuchi, M. Saito, M. Hashimoto, and T. Tanaka Chem. Lett. 1984 441 444
27. A.F. Abdel-Magid, K.G. Carson, B.D. Harris, C.A. Maryanoff, and R.D. Shah J. Org. Chem. 61 1996 3849 3862
28. T. Ruckle, B. Dubray, F. Hubler, and M. Mutter J. Pept. Sci. 5 1999 56 58
29. H. Schedel, and K. Burger Monatsh. Chem. 131 2000 1011 1018
30. M. Remko J. Phys. Chem. A 107 2003 720 725
31. I. Chataigner, C. Panel, H. Gérard, and S.R. Piettre Chem. Commun. 2007 3288 3290
32. S. anli, Y. Altun, N. anli, G. Alsancak, and J.L. Beltran J. Chem. Eng. Data 54 2009 3014 3021
33. K.C. Kumara Swamy, N.N. Bhuvan Kumar, E. Balaraman, and K.V.P. Pavan Kumar Chem. Rev. 109 2009 2551 2651
34. R.C. Roemmele, and H. Rapoport J. Org. Chem. 53 1988 2367 2371
35. D. Papaioannou, C. Athanassopoulos, V. Magafa, N. Karamanos, G. Stavropoulos, A. Napoli, G. Sindona, D.W. Aksnes, and G.W. Francis Acta Chem. Scand. 48 1994 324 333
36. C. Athanassopoulos, D. Papaioannou, A. Napoli, C. Siciliano, and G. Sindona J. Mass Spectrom. 30 1995 1284 1290
37. B.W. Clare, A. Scozzafava, and C.T. Supuran J. Med. Chem. 44 2001 2253 2258
38. S.M. Marques, E. Nuti, A. Rossello, C.T. Supuran, T. Tuccinardi, A. Martinelli, and M.A. Santos J. Med. Chem. 51 2008 7968 7979
39. L. Gavernet, J.E. Elvira, G.A. Samaja, V. Pastore, M. Sella Cravero, A. Enrique, G. Estiu, and L.E. Bruno-Blanch J. Med. Chem. 52 2009 1592 1601
40. T.H. Maren, and C.W. Conroy J. Biol. Chem. 268 1993 26233 26239
41. N. Koyanagi, T. Nagasu, F. Fujita, T. Watanabe, K. Tsukahara, Y. Funahashi, M. Fujita, T. Taguchi, H. Yoshino, and K. Kitoh Cancer Res. 54 1994 1702 1706
42. T. Owa, H. Yoshino, T. Okauchi, K. Yoshimatsu, Y. Ozawa, N.H. Sugi, T. Nagasu, N. Koyanagi, and K. Kitoh J. Med. Chem. 42 1999 3789 3799
43. A. Scozzafava, T. Owa, A. Mastrolorenzo, and C.T. Supuran Curr. Med. Chem. 10 2003 925 953
44. S.P. Gupta Chem. Rev. 107 2007 3042 3087
45. B.H. Fung, L.H. Kirschenbaum, and R. Hameed Clin. Ther. 22 2000 549 572
46. K.A. Ghosh, M.L. Swanson, H. Cho, S. Leschenko, A.K. Hussain, S. Kays, E.D. Walker, Y. Koh, and H. Mitsuya J. Med. Chem. 48 2005 3576 3585
47. M.C. Yeung, L.L. Klein, A.C. Flentge, T.J. Randolph, C. Zhao, H.S. Ming, D. Tatyana, S.S. Vincent, and J.D. Kempf Bioorg. Med. Chem. Lett. 15 2005 2275 2278
48. R. Mohan, M. Banerjee, A. Ray, T. Manna, L. Wilson, T. Owa, B. Bhattacharyya, and D. Panda Biochemistry 45 2006 5440 5449
49. S.P. Gupta, V. Maheswaran, V. Pande, and D. Kumar J. Enzyme Inhib. Med. Chem. 18 2003 7 13
50. E. Nuti, E. Orlandini, S. Nencetti, A. Rossello, A. Innocenti, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. 15 2007 2298 2311
51. D. Maclean, R. Hale, and M. Chen Org. Lett. 3 2001 2977 2980
52. Y. Hu, Z.-C. Chen, Z.-G. Le, and Q.-G. Zheng Org. Prep. Proced. Int. 36 2004 347 351
53. For Lewis acid assisted reactions see
54. M. Noji, T. Ohno, K. Fuji, N. Futaba, H. Tajima, and K. Ishii J. Org. Chem. 68 2003 9340 9347
55. V. Terrasson, S. Marque, M. Georgy, J.M. Campagne, and D. Prim Adv. Synth. Catal. 348 2006 2063 2067
56. C.R. Reddy, P.P. Madhabi, and A.S. Reddy Tetrahedron Lett. 48 2007 7169 7172
57. H. Qin, N. Yamagiwa, S. Matsunga, and M. Shibasaki Angew. Chem. 119 2007 413 417
58. Angew. Chem., Int. Ed. 46 2007 409 413
59. B. Sreedhar, P.S. Reddy, M.A. Reddy, B. Neelima, and R. Arundhathi Tetrahedron Lett. 48 2007 8174 8177
60. U. Jana, S. Maiti, and S. Biswas Tetrahedron Lett. 49 2008 858 862 For ruthenium-catalyzed processes see
61. M.H.S.A. Hamid, C.L. Allen, G.W. Lamb, A.C. Maxwell, H.C. Maytum, A.J.A. Watson, and J.M.J. Williams J. Am. Chem. Soc. 131 2009 1766 1774
62. F. Shi, M.K. Tse, S. Zhou, M. Pohl, J. Radnik, S. Hübner, K. Jähnisch, A. Brückner, and M. Beller J. Am. Chem. Soc. 131 2009 1775 1779
63. F. Shi, M.K. Tse, X. Cui, D. Gördes, D. Michalik, K. Thurow, Y. Deng, and M. Beller Angew. Chem. 121 2009 6026 6029
64. M.L. Di Gioia, A. Leggio, A. Le Pera, A. Liguori, A. Napoli, C. Siciliano, and G. Sindona J. Org. Chem. 68 2003 7416 7421
65. M.L. Di Gioia, A. Leggio, A. Liguori, and F. Perri J. Org. Chem. 72 2007 3723 3728
66. E. Belsito, M.L. Di Gioia, A. Greco, A. Leggio, A. Liguori, F. Perri, C. Siciliano, and M.C. Viscomi J. Org. Chem. 72 2007 4798 4802
67. M.L. Di Gioia, A. Leggio, A. Liguori, F. Perri, C. Siciliano, and M.C. Viscomi Amino Acids 38 2010 133 143
68. A. Leggio, A. Liguori, F. Perri, C. Siciliano, and M.C. Viscomi Chem. Biol. Drug Des. 73 2009 287 291
69. E.L. Belsito, R. De Marco, M.L. Di Gioia, A. Liguori, F. Perri, and M.C. Viscomi Eur. J. Org. Chem. 2010 4245 4252
70. S.C. Miller, and T.S. Scanlan J. Am. Chem. Soc. 119 1997 2301 2302
71. L. Antolini, L.P. Battaglia, G. Battistuzzi Gavioli, A. Bonamartini Corradi, G. Grandi, G. Marcotrigiano, L. Menabue, and G.C. Pellacani J. Am. Chem. Soc. 105 1983 4327 4332
72. L. Antolini, L.P. Battaglia, G. Battistuzzi Gavioli, A. Bonamartini Corradi, G. Grandi, G. Marcotrigiano, L. Menabue, and G.C. Pellacani J. Am. Chem. Soc. 105 1983 4333 4337
73. L.P. Battaglia, A. Bonamartini Corradi, G. Marcotrigiano, L. Menabue, and G.C. Pellacani Inorg. Chem. 22 1983 1902 1906
74. H. Zollinger Diazo Chemistry II - Aliphatic, Inorganic and Organometallic Compounds 1995 VCH Weinheim pp 138-143
75. A. Leggio, A. Liguori, A. Napoli, C. Siciliano, and G. Sindona J. Org. Chem. 66 2001 2246 2250
76. F. Hubler, T. Ruckle, L. Patiny, T. Muamba, J.F. Guichou, M. Mutter, and R. Wenger Tetrahedron Lett. 41 2000 7193 7196
77. F. Arndt Org. Synth. 2 1943 165 167