A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids

Journal of Organic Chemistry

Volumn 77, Issue 23, 2012, Pages 10575-10582

  Siciliano, Carlo ^a   De Marco, Rosaria ^a   Guidi, Ludovica Evelin ^a   Spinella, Mariagiovanna ^a   Liguori, Angelo ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

9-FLUORENYLMETHYL CHLOROFORMATE; ACID-LABILE; DIASTEREOMERIC; DIAZOKETONES; DIAZOMETHANES; FLASH COLUMN CHROMATOGRAPHY; FMOC-CL; L-ISOLEUCINE; ONE POT; ONE-POT PROCEDURES; PROTECTING GROUP; REACTION CONDITIONS; SIDE-CHAINS; SOLID PHASE PEPTIDE SYNTHESIS; TITLE COMPOUNDS;

CHLORINE COMPOUNDS;

AMINO ACIDS;

2,2,4,6,7 PENTAMETHYLDIHYDROBENZOFURAN 5 SULFONYL; ALPHA AMINO ACID; CARBONYL DERIVATIVE; DIAZOMETHANE; KETONE DERIVATIVE; N 9 FLUORENYLMETHYLOXYCARBONYL ALPHA AMINO DIAZOKETONE DERIVATIVE; N FMOC AMINO DIAZOKETONE DERIVATIVE; SULFONYLUREA; TERT BUTYLOXYCARBONYL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; ONE POT SYNTHESIS;

AMINO ACIDS; DIAZONIUM COMPOUNDS; DIPEPTIDES; FLUORENES; MOLECULAR STRUCTURE;

EID: 84870863725     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301657e     Document Type: Article

References (66)

1. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160
2. Sulikowski, G. A.; Lulu Cha, K.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169
3. Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577-6605 and references cited therein
4. Linder, M. R.; Podlech J. Org. Lett. 1999, 1, 869-871
5. Linder, M. R.; Podlech J. Org. Lett. 2001, 3, 1849-1851
6. Taubinger, A. A.; Fenske, D.; Podlech, J. Tetrahedron 2008, 64, 8659-8667
7. Guibourdenche, C.; Seebach, D.; Natt, F. Helv. Chim. Acta 1997, 80, 1-13
8. Marti, R. E.; Bleicher, K. H.; Bair, K. W. Tetrahedron Lett. 1997, 38, 6145-6148
9. Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187-206
10. Suresh Babu, V. V.; Gopi, H. N. Lett. Pept. Sci. 1999, 6, 173-178
11. Patil, B. S.; Vasanthakumar, G.-R.; Suresh Babu, V. V. Lett. Pept. Sci. 2002, 9, 231-233
12. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913-941
13. Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 2043-2066
14. Cole, D. C. Tetrahedron 1994, 50, 9517-9582
15. Podlech, J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 471-472
16. Podlech, J.; Seebach, D. Liebigs Ann. 1995, 1217-1228
17. Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121-1129
18. Apella, D. H.; Christianson, L. A.; Klein, D. A.; Powell, D. R.; Huang, X.; Barchi, J. J., Jr; Gellman, S. H. Nature 1997, 387, 381-384
19. Iso, Y.; Shindo, H.; Hamana, H. Tetrahedron 2000, 56, 5353-5361
20. Arndt, F.; Eistert, B.; Partale, W. Ber. Dtsch. Chem. Ges. 1927, 60B, 1364-1370
21. Arndt, F.; Eistert, B.; Amende, J. Ber. Dtsch. Chem. Ges. 1928, 61B, 1949
22. Carpino, L. A.; Beyermann, M.; Wenschuh, H.; Bienert, M. Acc. Chem. Res. 1996, 29, 268-274
23. Wang, J.; Hou, Y. J. Chem. Soc., Perkin Trans 1 1998, 1919-1924
24. Ye, T.; McKervey, A. M. Tetrahedron 1992, 48, 8007-8022
25. Heinsoo, A.; Raidaru, G.; Linask, K.; Jarv, J.; Zetterstrom, M.; Langel, U. Tetrahedron: Asymmetry 1995, 6, 2245-2247
26. Ananda, K.; Gopi, H. N.; Suresh Babu, V. V. J. Pept. Res. 2000, 55, 289-294
27. Plucinska, K.; Liberek, B. Tetrahedron 1987, 43, 3509-3517
28. Ellmerer-Müller, E. P.; Brössner, D.; Maslouh, N.; Takó, A. Helv. Chim. Acta 1998, 81, 59-65
29. Tantry, S. J.; Vasanthakumar, G.-R.; Suresh Babu, V. V. Lett. Pept. Sci. 2003, 10, 51-55
30. Tantry, S. J.; Suresh Babu, V. V. Lett. Pept. Sci. 2003, 10, 655-662
31. Bodanszky, M.; Du Vigneaud, V. Nature 1959, 183, 1324-1325
32. Pless, J.; Boissonnas, R. A. Helv. Chim. Acta 1963, 46, 1609-1625
33. Sandrin, E.; Boissonnas, R. A. Helv. Chim. Acta 1963, 46, 1637-1669
34. Anderson, G. W.; Zimmermann, J. E.; Callahan, F. M. J. Am. Chem. Soc. 1963, 85, 3039
35. Johnson, B. J.; Trask, E. G. J. Org. Chem. 1968, 33, 4521-4525
36. Kisfaludy, L.; Low, M.; Nyeki, O.; Szirtes, T.; Schon, I. Liebigs Ann. Chem. 1973, 1421-1429
37. Anderson, G. W.; Zimmermann, J. E.; Callahan, F. M. J. Am. Chem. Soc. 1964, 86, 1839-1842
38. Pettit, G.; Nelson, P. S. Can. J. Chem. 1986, 64, 2097-3102
39. Hodson, D.; Holt, G.; Wall, D. K. J. Chem. Soc. C 1970, 971-973
40. Vasanthakumar, G.-R.; Suresh Babu, V. V. J. Pept. Res. 2003, 61, 230-236
41. Pace, V.; Verniest, G.; Sinisterra, J.-V.; Alcántara, A. R.; De Kimpe, N. J. Org. Chem. 2010, 75, 5760-5763
42. Cuevas-Yañez, E.; García, M. A.; de la Mora, M. A.; Muchowski, J. M.; Cruz-Almanza, R. Tetrahedron Lett. 2003, 44, 4815-4817
43. Saraireh, I. A. M. Tetrahedron Lett. 2012, 53, 2023-2025
44. Cvejn, D.; KlimesÌová, V.; BuresÌ, F. Cent. Eur. J. Org. Chem. 2012, 10, 1681-1687
45. Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1980, 21, 4461-4462
46. Kuroda, S.; Akahane, A.; Itani, H.; Nishimura, S.; Durkin, K.; Tenda, Y.; Sakane, K. Bioorg. Med. Chem. 2000, 8, 55-64
47. Cesar, J.; Dolenc, M. S. Tetrahedron Lett. 2001, 42, 7099-7102
48. Leggio, A.; Liguori, A.; Napoli, A.; Siciliano, C.; Sindona, G. Eur. J. Org. Chem. 2000, 573-575
49. Di Gioia, M. L.; Leggio, A.; Liguori, A.; Napoli, A.; Siciliano, C.; Sindona, G. J. Org. Chem. 2001, 66, 7002-7007
50. Di Gioia, M. L.; Leggio, A.; Le Pera, A.; Liguori, A.; Perri, F.; Siciliano, C. Eur. J. Org. Chem. 2004, 4437-4441
51. Di Gioia, M. L.; Leggio, A.; Liguori, A.; Siciliano, C.; Sindona, G. J. Pept. Res. 2004, 63, 383-387
52. Leggio, A.; Liguori, A.; Procopio, A.; Sindona, G. J. Chem. Soc., Perkin Trans. 1 1997, 1969-1971
53. Di Gioia, M. L.; Leggio, A.; Le Pera, A.; Liguori, A.; Napoli, A.; Siciliano, C.; Sindona, G. J. Org. Chem. 2003, 68, 7416
54. Belsito, E.; Di Gioia, M. L.; Greco, A.; Leggio, A.; Liguori, A.; Perri, F.; Siciliano, C.; Viscomi, M. C. J. Org. Chem. 2007, 72, 4798-4802
55. Kantharaju, K.; Suresh Babu, V. V. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43, 2152-2158
56. Arndt, F. Org. Synth. 1943, 2, 165-168
57. Carpino, L. A.; Han, G. Y. J. Am. Chem. Soc. 1970, 92, 5748-5749
58. Carpino, L. A.; Han, G. Y. J. Org. Chem. 1972, 37, 3404-3409
59. Carpino, L. A. Acc. Chem. Res. 1987, 20, 401-407
60. Seela, F.; Wenzel, T. Helv. Chim. Acta 1992, 75, 1111-1122
61. Mérette, S. A. M.; Burd, A. P.; Deadman, J. J. Tetrahedron Lett. 1999, 40, 753-754
62. Hong, Y.; Liao, B.; Liu, B.; Xiong., F. Chin. J. Org. Chem. 2000, 20, 367-371
63. De Marco, R.; Di Gioia, M. L.; Leggio, A.; Liguori, A.; Perri, F.; Siciliano, C.; Viscomi, M. C. Amino Acids 2010, 38, 691-700
64. De Marco, R.; Di Gioia, M. L.; Liguori, A.; Perri, F.; Siciliano, C.; Spinella, M. Tetrahedron 2011, 67, 9708-9714
65. Di Donna, L.; Benabdelkamel, H.; Mazzotti, F.; Napoli, A.; Nardi, M.; Sindona, G. Anal. Chem. 2011, 83, 1990-1995
66. Napoli, A.; Athanassopoulos, C. M.; Moschidis, P.; Aiello, D.; Di Donna, L.; Mazzotti, F.; Sindona, G. Anal. Chem. 2010, 82, 5552-5560