Intermolecular alkyl radical addition to the carbon-nitrogen double bond of oxime ethers and hydrazones

Tetrahedron

Volumn 54, Issue 38, 1998, Pages 11431-11444

  Miyabe, Hideto ^a   Shibata, Ryouhei ^a   Sangawa, Masato ^a   Ushiro, Chikage ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CARBON NITROGEN MONOCYCLE; ETHER DERIVATIVE; HYDRAZONE DERIVATIVE; IMINE; OXIME;

ALKYLATION; ARTICLE; BASE PAIRING; CHEMICAL ANALYSIS; CHEMICAL REACTION; PH; PRIORITY JOURNAL; THIN LAYER CHROMATOGRAPHY;

EID: 0032541555     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00706-6     Document Type: Article

References (65)

1. 1. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry.; Translated by Lomas, J., John Wiley & Sons: New York, 1995.
2. For recent reviews, see: a) Ryu, I.; Sonoda, N.; Curran. D. P. Chem. Rev. 1996, 96, 177-194.
3. b) Snider, B. B. Chem. Rev. 1996, 96, 339-364.
4. c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301-856.
5. 2. a) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633.
6. b) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199.
7. 3. a) Kim, S.; Lee, I. Y.; Yoon, J. Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139.
8. b) Kim, S.; Yoon, J.-Y.; Lee, I. Y. Synlett 1997, 475-476.
9. 4. Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789-1790.
10. 5. a) Risch, N.; Arend, N. Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds., Thieme: Stuttugart, New York, 1996; vol. 3; pp. 1833-2009.
11. b) Volkmann, R. A. Comprehensive Organic Synthesis; Trost B. M. Ed., Pergamon Press: Oxford, 1991; vol. 1; pp.355-396.
12. For some recent reviews: a) Enders, D.; Reinhold, U. Tetrahedron Asymmetry 1997, 8, 1895-1946.
13. b) Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1997, 999-1004.
14. For some recent examples of the addition of organometallic carbon nucleophiles to the oxime ether: a) Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. Synlett 1997, 659-660.
15. b) Marco, J. A.; Carda, M.; Murga, J.; González, F.; Falomir, E. Tetrahedron Lett. 1997, 38, 1841-1844.
16. c) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273-5276.
17. d) Dieter, R. K.; Datar, R. Can. J. Chem. 1993, 71, 814-823.
18. e) Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431-5446.
19. f) Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415-5423.
20. g) Rodriques, K. E.; Basha, A.; Summers, J. B.; Brooks, D. W. Tetrahedron Lett. 1988, 29, 3455-3458.
21. h) Itsuno, S.; Miyazaki, K.; Ito, K. Tetrahedron Lett. 1986, 27, 3033-3036.
22. i) Corey, E. J.; Niimura, K.; Konishi, Y.; Hashimoto, S.; Hamada, Y. Tetrahedron Lett. 1986, 27, 2199-2202.
23. j) Pirie, D. K.; Welch, W. M.; Weeks, P. D.; Volkmann, R. A. Tetrahedron Lett. 1986, 27, 1549-1552.
24. k) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707-4710.
25. l) Fiaud, J.-C.; Kagan, H. B. Tetrahedron Lett. 1971, 1019-1022.
26. 6. A part of this work appeared in preliminary communication: Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634.
27. 7. For recent review: Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543-17594.
28. For selected recent examples of the intramolecular radical addition to oxime ethers: a) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550.
29. b) Marco-Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209.
30. c) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367.
31. d) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399.
32. e) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011.
33. f) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365-1368.
34. g) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888.
35. h) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932.
36. i) Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
37. For selected recent examples of the intramolecular radical addition to hydrazones: a) Grissom, J. W.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603-626.
38. b) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448.
39. c) Bernard-Henriet, C. D.; Grimaldi, J. R.; Hatem, M. Tetrahedron Lett. 1994, 35, 3699-3702.
40. d) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron Lett. 1994, 35, 6369-6372.
41. e) Belletire, J. L.; Hagedorn, C. E.; Ho, D. M.; Krause, J. Tetrahedron Lett. 1993, 34, 797-800.
42. f) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882-9883.
43. 8. a) Miyabe, H.; Torieda, M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. J. Org. Chem. 1998, 63, 4397-4407.
44. b) Miyabe, H.; Kanehira, S.; Kume, K.; Kandori, H.; Naito, T. Tetrahedron 1998, 54, 5883-5892.
45. c) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580-582.
46. d) Naito, T.; Torieda, M.; Tajiri, K.; Ninomiya, I.; Kiguchi, T. Chem. Pharm. Bull. 1996, 44, 624-626.
47. e) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256.
48. f) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206.
49. 9. a) Kim, S.; Kim, Y.; Yoon, K. S. Tetrahedron Lett. 1997, 38, 2487-2490.
50. b) Kim, S.; Yoon, K. S.; Kim, Y. S. Tetrahedron Lett. 1997, 38, 73-80.
51. 10. For recent examples employing Lewis acid in radical reactions: Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 274-276 and references cited therein.
52. 11. Stack, J. G.; Curran, D. P.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1991, 113, 5918-5920.
53. 12. Fung, N. Y. M.; Mayo, P.; Schauble, J. H.; Weedon, A. C. J. Org. Chem. 1978, 43, 3977-3979.
54. 13. a) Guindon, Y.; Guérin, B.; Chabot C.; Ogilvie, W. J. Am. Chem. Soc. 1996, 118, 12528-12535 and references cited therein.
55. b) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K., Bull. Chem. Soc. Jpn. 1989, 62, 143-147.
56. c) Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403-409 and references cited therein.
57. 14. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431-5440.
58. 15. Ikeda, K.; Yoshinaga, Y.; Achiwa, K.; Sekiya, M. Chem. Lett. 1984, 369-370.
59. 16. Kamitori, Y.; Hojo, M.; Masuda, R.; Fujitani, T.; Ohara, S.; Yokoyama, T. J. Org. Chem. 1988, 53, 129-135.
60. 17. Dugat, D.; Just, G.; Sahoo, S. Can. J. Chem. 1987, 88-93.
61. 18. Bashiardes, G.; Bodwell, G. J.; Davies, S. G. J. Chem. Soc., PertinTrans 1 1993, 459-469.
62. 19. Haley, M. F.; Yates, K. J. Org. Chem. 1987, 52, 1825-1830.
63. 20. Huang, F.-C.; Shoupe, T. S.; Lin, C. J.; Lee, T. D. Y.; Chan, W.-K.; Tan, J.; Schnapper, M.; Suh, J. T.; Gordon, R. J.; Sonnio, P. A.; Sutherland, C. A.; Van Inwegen, R. G. J. Med. Chem. 1989, 32, 1836-1842.
64. 21. Shimizu, K.; Nakayama, K.; Akiyama, M. Bull. Chem. Soc. Jpn. 1984, 57, 2456-2462.
65. 22. Isozaki, M.; Nakazawa, K.; Kasukawa, H. Jpn. Kokai Tokkyo Koho JP 08,291,127 [96,291,127] (CI.C07C259/10) [Chem. Abstr. 1997, 126, 74552Y.]