Tandem radical decarboxylation-oxidation of amino acids: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping

Journal of Organic Chemistry

Volumn 65, Issue 16, 2000, Pages 4930-4937

  Boto, Alicia ^a   Hernández, Rosendo ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINO ACID; AMINOLACTONE; BENZENE DERIVATIVE; CARBON DIOXIDE; N ACYLIMINIUM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; URONIC ACID;

AMINO ACID SEQUENCE; ARTICLE; DECARBOXYLATION; HYDROXYLATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343167391     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000356t     Document Type: Article

References (84)

1. (a) Griesbeck, A. G.; Kramer, W.; Oelgemoller, M. Synlett 1999, 1169-1178.
2. (b) Fontana, F.; Minisci, F.; Barbosa, M. C. N.; Vismara, E. J. Org. Chem. 1991, 56, 2866-2869.
3. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413-1432.
4. Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489-519.
5. (e) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
6. (f) Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901-3924. For recent examples of oxidative decarboxylation, see:
7. (g) Anger, T.; Graalmann, O.; Schröder, H.; Gerke, R.; Kaiser, U.; Fitjer, L.; Noltemeyer, M. Tetrahedron 1998, 54, 10713-10720.
8. (h) Endo, K.; Hirayama, K.; Aota, Y.; Seya, K.; Asakura, H.; Hisamichi, K. Heterocycles 1998, 47, 865-870.
9. Paradkar, V. M.; Latham, T. B.; Demko, D. M. Synlett 1995, 1059-1060.
10. (j) Graven, A.; Jorgensen, K. A.; Dahl, S.; Stanczak, A. J. Org. Chem. 1994, 59, 3543-3546.
11. (a) Boto, A.; Hernández, R.; Suárez, E. Tetrahedron Lett. 1999, 40, 5945-5948.
12. (b) Francisco, C. G.; González, C. C.; Suárez, E. Tetrahedron Lett. 1997, 38, 4141-4144.
13. Francisco, C. G.; Freire, R.; Rodríguez, M. S.; Suárez, E. Tetrahedron Lett. 1995, 36, 2141-2144.
14. Concepción, J. I.; Francisco, C. G.; Freire, R.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1986, 51, 402-404.
15. For others decarboxylations of amino acids, see: (a) Corcoran, R. C.; Green, J. M. Tetrahedron Lett. 1990, 31, 6827-6830.
16. (b) Seebach, D.; Charczuk, R.; Gerber, C.; Renaud, P.; Berner, H.; Schneider, H. Helv. Chim. Acta 1989, 72, 401-425.
17. Gledhill, A. P.; McCall, C. J.; Threadgill, M. D. J. Org. Chem. 1986, 51, 3196-3201 and references therein.
18. For general reviews on N-acyliminium ions, see: (a) Padwa, A. Chem. Commun. 1998, 1417-1424.
19. (b) De Koning, H.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdan, 1993; Vol. 13, pp 473-518.
20. De Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie (Houben-Weyl); Thieme: Stuttgart, Germany, 1995; Vol. E 21b, pp 1953-2009.
21. Overman, L. E. Acc. Chem. Res. 1992, 25, 352-359.
22. (e) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, pp 1047-1082.
23. (f) Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, pp 1007-1046.
24. (g) De Koning, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, pp 271-339.
25. (h) Hart, D. J. In The Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1988; Vol. 6, pp 227-296.
26. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416.
27. (j) Zaugg, H. E. Synthesis 1984, 85-110.
28. (k) Zaugg, H. E. Synthesis 1984, 181-212.
29. Schoemaker, H. E.; Boer-Terpstra, Tj.; Dijkink, J.; Speckamp, W. N. Tetrahedron 1980, 36, 143-148.
30. For some recent examples, see: (a) Remuson, R.; Chalard, P.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
31. (b) Beyersbergen van Henegouwen, W. G.; Fieseler, R. M.; Rutjes, F. P. J. T.; Hiemstra, H. Angew. Chem., Int. Ed. 1999, 38, 2214-2217.
32. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395-7400.
33. Luker, T.; Hiemstra, H.; H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
34. (e) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314-323.
35. (f) Rigo, B.; El Ghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485-486.
36. (g) Corey, E. J.; Gin, D. Y.; Kania, R. S. J Am. Chem. Soc. 1996, 118, 9202-9203.
37. (h) Lögers, M.; Overman, L. E.; Welmaker, G. S. J Am. Chem. Soc. 1995, 117, 9139-9150.
38. Overman, L. E.; Rabinowitz, M. H. Renhowe, P. A. J Am. Chem. Soc. 1995, 117, 2657-2658.
39. (j) Newcombe, N. J.; Ya, F.; Vijn, R. J.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1994 767-768.
40. (a) Yamaguchi, R.; Tanaka, M.; Matsuda, T.; Fujita, K-i. Chem. Commun. 1999, 2213-2214 and references therein.
41. (b) Itoh, T.; Nagata, K.; Miyazaki, M.; Ohsawa, A. Synlett 1999, 1154-1156 and references therein.
42. Reviews on electroorganic synthesis: (a) Utley, J. Chem. Soc. Rev. 1997, 157-167.
43. (b) Shono, T. Tetrahedron 1984, 811-850.
44. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991.
45. (a) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989.
46. (b) Remuzon, P. Tetrahedron 1996, 52, 13803-13835
47. Parsons, A. F. Tetrahedron 1996, 52, 4149-4174.
48. Product 1b: Yamada, K.; Takeda, M.; Iwakuma, T. J. Chem. Soc., Perkin Trans. 1 1983, 265-270.
49. (e) Product 1c: Nakai, H.; Sato, Y.; Mizoguchi, T. Synthesis 1982, 141-143.
50. (f) Product 1e is commercially available from Aldrich, but it was prepared from proline: Furniss, B. S.; Hamaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry; Addison-Wealey-Longman: Essex, 1996; p 762.
51. (g) Product 1f: Irie, H.; Nakanishi, H.; Fujii, N.; Mizuno, Y.; Fushimi, T.; Funakoshi, S.; Yahima, H. Chem. Lett. 1980, 705-708.
52. (h) For a related synthesis to compound 5, see: Robinson, J. K.; Lee, V.; Claridge, T. D. W.; Baldwin, J. E.; Schofield, C. J. Tetrahedron 1998, 54, 981-996.
53. (a) Hernández, R.; Marrero, J. J.; Melián, D.; Suárez, E. Tetrahedron Lett. 1988, 29, 6661-6664.
54. (b) Ciufolini, M. A.; Wood, C. Y. Tetrahedron Lett. 1986, 27, 5085-5088.
55. For reviews on Ritter-like reactions: (a) Bishop, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 261-300. Addition of acetonitrile to oxycarbenium ions:
56. (b) Kita, Y.; Shibata, N.; Kawano, N.; Yoshida, N.; Matsumoto, K.; Takebe, Y. J. Chem. Soc., Perkin Trans. 1 1996, 2321-2329.
57. For related ω-hydroxy aldehyde/hemiacetal tautomerism see: El-Khadem, H. S. Carbohydrate Chemistry: Monosacharides and Their Oligomers; Academic Press: San Diego, CA, 1988; pp 15-56.
58. Karle, I. L.; Pramanik, A.; Banerjee, A.; Bhattacharjya, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 9087-9095 and references therein.
59. (a) Bols, M. Acc. Chem. Res. 1998, 31, 1-8.
60. (b) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135-162.
61. Look, G. C.; Fotsch, C. H.; Wong, C. H. Acc. Chem. Res. 1993, 26, 182-190 and references therein.
62. Product 13: (a) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058-4067. Product 14:
63. (b) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176.
64. (a) Dictionary of Alkaloids; Southon, I. W., Buckingham, J., Eds; Chapman and Hall: London, 1989.
65. (b) Murakami, M.; Ishida, K.; Okino, T.; Okita, Y.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 2785-2788 and references therein.
66. Yoshida, J-i.; Suga, S.; Suzuki, S.; Kinomura, N.; Yamamoto, A.; Fujiwara, K. J. Am. Chem. Soc. 1999, 121, 9546-9549.
67. For closely related compounds, see: (a) Martin, S. F.; Corbett, J. W. Synthesis 1992, 55-57.
68. (b) Rassu, G.; Carta, P.; Pinna, L.; Battistini, L.; Zanardi, F.; Acquotti, D.; Casiraghi, G. Eur. J. Org. Chem. 1999, 1395-1400. For reviews of trialkylsilyloxyfurans, see:
69. Casiraghi, G.; Rassu, G. Synthesis 1995, 607-626.
70. Rassu, G.; Zanardi, F.; Battistini, L.; Cashiraghi, G. Synlett, 1999, 1333-1350. For other reviews with related strategies, see:
71. (e) Hanessian, S. Tetrahedron 1997, 53, 12789-12854.
72. (f) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872.
73. Lee, I. S.; Kim, S. H.; Jung, S. H.; Lee, S. J.; Park, H. Hetereocycles 1994, 37, 303-309.
74. MMX force field as implemented in PCMODEL (v. 4.0), Serena Software, Bloomington IN, 47402-3076.
75. Goswami, R.; Moloney, M. G. Chem. Commun. 1999, 2333-2334.
76. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783-2792.
77. For a similar result, see: Renaud, P.; Seebach, D. Helv. Chim. Acta 1986, 69, 1704-1710.
78. (a) Dorta, R. L.; Francisco, C. G.; Suarez, E. J. Chem. Soc., Chem. Commun. 1989, 1168-1170.
79. (b) de Armas, P.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez. E. J. Chem. Soc., Perkin Trans. 1 1988, 3255-3265.
80. Carrau, R.; Hernández, R.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1987, 937-943.
81. Hernández, R.; Medina, M. C.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1987, 28, 2533-2536.
82. (e) de Armas, P.; Carrau, R.; Concepción, J. L; Francisco, C. G.; Hernández, R.; Suárez, E. Tetrahedron Lett. 1985, 26, 2493-2496.
83. (f) Betancor, C.; Concepción, J. I.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1983, 48, 4430-4432.
84. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.