Synthesis of acylnitroso intermediates and their synthetic applications

Mini-Reviews in Organic Chemistry

Volumn 2, Issue 2, 2005, Pages 157-175

  Iwasa, Seiji ^a   Fakhruddin, Ahmad ^a   Nishiyama, Hisao ^b  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

Acylnitroso intermediate; Asymmetric synthesis; Ene reaction; Hetero Diels Alder reaction; Hydroxamic acid; Total synthesis

Indexed keywords

OLEFINS; REACTION INTERMEDIATES;

ACYLNITROSO INTERMEDIATE; ASYMMETRIC SYNTHESIS; ENE REACTION; HETERO DIELS-ALDER REACTION; HYDROXAMIC ACIDS; NATURAL PRODUCTS; ORGANIC MOLECULES; REACTIVE SPECIES; SYNTHETIC APPLICATION; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

EID: 37249001503     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570193053544445     Document Type: Review

References (86)

1. For articles on the synthetic application of acylnitroso intermediates, see: a) Tsoungas, P. G. Heterocycles 2002, 57, 1149-1151;
2. b) Kirby, G. W.; McLean, D. J. Chem. Soc. Perkin Trans. 1, 1985, 1443-1445;
3. c) Keck, G. E.; Nickell, D. G. J. Am. Chem. Soc. 1980, 102, 3632-3634;
4. d) Shishido, Y.; Kibayashi, C. J. Chem. Soc. Chem. Commun. 1991, 18, 1237-1239;
5. e) Narase, M.; Aoyogi, S.; Kibayashi, C. J. Org Chem. 1994, 59, 1358-1364;
6. f) Keck, G. E.; Romer, D. R. J. Org. Chem. 1993, 58, 6083-6089;
7. g) Baldwin, J. E.; Otsuka, M.; Wallace, P. M. Tetrahedron 1986, 42, 3097-3110;
8. h) Baldwin, J. E.; Bailey, P. D.; Gallacher, G.; Otsuka, M.; Singleton, K. A.; Wallace, P. M.; Prout, K.; Wolf, W. M. Tetrahedron 1984, 40, 3695-3708;
9. i) Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayshi, C. J. Org. Chem. 1998, 63, 8397-8406;
10. j) Duvillard, I. C.; Berrien, J. F.; Ghosez, L.; Husson, H. P.; Royer, J. Tetrahedron 2000, 56, 3763-3769;
11. k) Li, J.; Lang, F.; Ganem, B. J Org. Chem. 1998, 63, 3403-3410;
12. l) Ghosh, A.; Miller, M. J. Tetrahedron Lett. 1995, 36, 6399-6402;
13. m) Naruse, M.; Aoyagi, S.; Kibayshi, C. J. Chem. Soc. Perkin Trans. 1, 1996, 1113-1124;
14. n) Soulie, J.; Bezer, J. K.; Muiller, B.; Lallemand, J. Y. Tetrahedron Lett. 1995, 36, 9495-9488;
15. o) Aoyagi, S.; Shishido, Y.; Kibayashi, C. Tetrahedron Lett. 1991, 32, 4325-4328;
16. p) Defoin, A.; Fritz, H.; Geffroy, G.; Streith, J. Tetrahedron Lett. 1986, 27. 4727-4730;
17. q) Fritz, H.; Henlin, J. M.; Riesen, A.; Tschamber, T.; Zehnder, M.; Streith, J. Helv. Chim. Acta 1988, 71, 922-834;
18. r) Jung, M.; Offenbacher, G.; Retey, J. Helv. Chim. Acta 1983, 66, 1915-1921;
19. s) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592;
20. t) Reddy, A. S.; Kumar, M. S.; Reddy, G. R. Tetrahedron Lett. 2000, 41, 6285-6288;
21. u) Rpper, A. G.; Procter, G.; Voyle, M. Chem.Commun, 2002, 10, 1066-1067;
22. v) Stark, C. M. J. Am. Chem. Soc. 1971, 93, 195-199.
23. Surman, M. D.; Miller, M. J. Org. Lett. 2001, 3, 519-521.
24. For reviews, see: x) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Pergamon Press: San Diego, 1987;
25. y) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press; Oxford, 1990.
26. Kirby, G. W. Chem. Soc. Rev. 1977, 6, 12-22.
27. Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3113-3115.
28. Voget, P. F.; Miller, M. J. Tetrahedron 1998, 54, 1323-1342.
29. a) Iwasa, S.; Tajima, K.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 5897-5899;
30. b) Iwasa, S.; Fakhruddin, A.; Tsukamoto, Y.; Kameyama, M.; Nishiyama, H. Tetrahedron Lett. 2002, 43, 6159-6161.
31. Quadrelli, P.; Invernizzi, A. G.; Caramella, P. Tetrahedron Lett. 1996, 37, 1909-1910.
32. Keck, G. E.; Webb, R. R.; Yates, J. B. Tetrahedron 1981, 37, 4007-4016.
33. O'Bannon, P. E.; Sulzle, D.; Schawrz, H. Helv. Chim. Acta 1991, 74, 2068-2072.
34. Cohen, A. D.; Zeng, B. B.; King, S. B.; Toscano, J. P. J. Am. Chem. Soc. Commun. 2003, 125, 1444-1445.
35. Miller, M. J. Chem. Rev. 1989, 89, 1563-1579.
36. a) Tamika, K.; Ogita, T.; Tanzawa, K.; Sugimura, Y. Tetrahedron Lett. 1993, 34, 683-686;
37. b) Altenburger, J. M.; Mioskowski, C.; D'Orchymont, H.; Schirlin D.; Schalk, C.; Tarnus, C. Tetrahedron Lett. 1992, 33, 5055-5058;
38. c) Staszak, M. A.; Doecke, C. W. Tetrahedron Lett. 1994, 35, 6021;
39. d) Ando, W.; Tsumaki, H. Synth. Commun. 1983, 13, 1053.
40. Sandler, S. R.; Karo, W. Organic Functional group preparations; Academic Press: New York 1972; Vol. 3, p. 411.
41. Reddy, A. S.; Kumar, M. S.; Reddy, G. R. Tetrahedron Lett. 2000, 41, 6285-6288.
42. Dhuru, S. P.; Salunkhe, M. M. J. Chinese Chem. Soc. 2000, 47, 1007-1008.
43. Sibi, M. P.; Hasegawa, H.; Ghorpade, S. R. Org. Lett. 2002, 4, 3343-3346.
44. a) Floyd, C. D.; Lewis, C. N.; Patal, S R.; Whittaker, M. Tetrahedron Lett. 1996, 37, 8045-8048;
45. b) Richter, L. S.; Desai, M. C. Tetrahedron Lett. 1997, 38, 321-322;
46. c) Chen, J. J.; Spatola, A. F. Tetrahedron Lett. 1997, 38, 1511-1514.
47. Giacomelli, G.; Porcheddu, A.; Salaris, M. Org. Lett. 2003, 5, 2715-2717.
48. Dao, L. H.; Dust, J. M.; Mackay, D.; Watson, K. N. Can. J. Chem. 1979, 57, 1712-1719.
49. Jenkins, N. E.; Ware, Jr., R. W.; Atkinson, R. N.; King, S. B. Synthetic Commun. 2000, 30, 947-953.
50. Davey, M. H.; Lee, V. Y.; Miller, R. D.; Marks, T. J. J. Org. Chem. 1999, 64, 4976-4979.
51. Quadrelli, P.; Inverizzi, A. G.; Caramella, P. Tetrahedron Lett. 1996, 37, 1909-1912.
52. Flower, K. R.; Lightfoot, A. P.; Wan, H.; Whiting, A. J. Chem. Soc. Perkin Trans. 1, 2002, 2058-2064.
53. Strukul, G. Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Kluwer Academic: Dordrecht, 1992; Vol. 9, p. 6.
54. Breithalle, E. G.; Fallis, A. G. J. Org. Chem. 1978, 43, 1964.
55. Sparks, S. M.; Vagas, J. D.; Shea, K. J. Org. Lett. 2000, 2, 1473-1475.
56. Chow, C. P.; Shen, K. J.; Sparks, S. M. Org. Lett. 2002, 4, 2637-2640.
57. Surman, M. D.; Miller, M. J. J. Org. Chem. 2001, 66, 2466-2469.
58. Sur-man, M. D.; Mulvihill, M. J.; Miller, M. J. Org. Lett. 2002, 4, 139-141.
59. Ellis, J. M.; King, S. B. Tetrahedron Lett. 2002, 43, 5833-5835.
60. Keck, G. E.; Webb, R. R.; Yates, J. B. Tetrahedron 1981, 37, 4007-4016.
61. Keck, G.E.; Webb, R.R. J. Am. Chem. Soc. 1981, 103, 3174-3175.
62. a) Corrie, J. E. T.; Kirby, G. W.; Mackinnon, J. W. M. J. Chem. Soc. Perkin Trans. 1, 1985, 883-886;
63. b) Kirby, G. W.; McGuigan, H.; McLean, D. J. Chem. Soc. Perkin Trans. 1, 1985, 1961-1966;
64. c) Ref, 31.
65. a) Quadrelli, P.; Mella, M.; Caramella, P. Tetrahedron Lett. 1998, 39, 3233-3236;
66. b) Quadrelli, P.; Mella, M.; Caramella, P. Tetrahedron Lett. 1999, 40, 797-800.
67. Adam, W.; Bottke, N.; Krebs, O.; Saha-Moler, C. R. Eur. J. Org. Chem. 1999, 1963-1965.
68. Kirby, G. W.; McGuigan, H.; McLean, D. J. Chem. Soc. Perkin Trans. 1, 1985, 1961-1966.
69. Ritter, A. R.; Miller, M. J. Tetrahedron Lett. 1994, 35, 9379-9382.
70. Baldwin, J. E.; Bailey, P. D.; Gallagher, G.; Singleton, K. A.; Wallace, P. M. J. Chem. Soc. Chem. Comm. 1983, 19, 1049.
71. Kirby, G. W.; Nazeer, M. Tetrahedron Lett. 1988, 29, 6173-6174.
72. Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 33, 3583-3586.
73. a) Defoin, A.; Schemidlin, C.; Streith, J. Tetrahedron Lett. 1984, 25, 4515-4518;
74. b) Defoin, A.; Fritz, H.; Gefferoy, G; Streith, J. Helv. Chim. Acta 1988, 71, 1642-1658;
75. c) Defoin, A.; Fritz, H.; Schmidlin, C; Streith, J. Helv. Chim. Acta 1987, 70, 554-569.
76. Defoin, A.; Pires, J.; Streith, J. Synlett 1991, 417-419.
77. Gouverneur, V.; Ghosez, L. Tetrahedron Asymmetry 1990, 1, 363-366.
78. a) Martin, S. F.; Toso, H. H. Heterocycles 1993, 35, 95-89;
79. b) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108-5115.
80. a) Burkholder, T. P.; Fuchs, P. L. J. Am. Chem. Soc. 1988, 110, 2341-1342;
81. b) Burkholder, T. P.; Fuchs, P. L. J. Am. Chem. Soc. 1990, 112, 9601-9613.
82. Nakagawa, H.; Sugahara, T.; Ogasawara, K. Org. Lett. 2000, 2, 3181-3183.
83. a) Ozawa, T.; Aoyagi, S; Yjbayashi, C. Org. Lett. 2000, 2, 2955-2958;
84. b) Ozawa, T.; Aoyagi, S; Kibayashi, C. J. Org. Chem. 2001, 66, 3338-3347.
85. Mineno,T.; Miller, M. J. J. Org. Chem. 2003, 68, 6591-9596.
86. Clark, R. D.; Souchet, M. Tetrahedron Lett. 1990, 31, 193-196.