Radical addition of ethers to imines initiated by dimethylzinc

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3509-3511

  Yamada, Ken Ichi ^a   Fujihara, Hidetaka ^a   Yamamoto, Yasutomo ^a   Miwa, Yoshihisa ^a   Taga, Tooru ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0013323218     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0266572     Document Type: Article

References (43)

1. (a) Hasegawa, M.; Taniyama, D.; Tomioka, K. Tetrahedron 2000, 56, 10153-10158.
2. (b) Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron Lett. 2000, 41, 5533-5536.
3. (c) Kambara, T.; Tomioka, K. J. Org. Chem. 1999, 64, 9282-9285.
4. (d) Tomioka, K. Synthesis 1990, 541-549.
5. (a) Nagai, K.; Fujihara, H.; Kuriyama, M.; Yamada, K.; Tomioka, K. Chem. Lett. 2002, 8-9.
6. (b) Fujihara, H.; Nagai, K.; Tomioka, K. J. Am. Chem. Soc. 2000, 122, 12055-12056.
7. Radical generation with diethylzinc involving halogen abstraction has been reported: (a) Bertrand, M. P.; Coantic, S.; Feray, L.; Nouguier, R.; Perfetti, P. Tetrahedron 2000, 56, 3951-3961.
8. (b) Bertrand, M. P.; Feray, L., Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189-9193.
9. (c) Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. Synlett 1999, 1148-1150.
10. (d) Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335-6336.
11. For reviews of radical addition to C=N bonds, sec: (a) Ishibashi, H.; Sato, T.; Ikeda, M. Synthesis 2002, 695-713.
12. (b) Friestad, G. K. Tetrahedron 2001, 57, 5461-5496.
13. (c) Naito, T. Heterocycles 1999, 50, 505-541.
14. (d) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543-17594. For other excellent reviews of radical reactions, see:
15. (e) Yet, L. Tetrahedron 1999, 55, 9349-9403.
16. (f) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991-2069.
17. (g) Giese B. In Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Organic Chemistry Series; Baldwin, J. E., Ed.; Pergamon Press: Elmsford, NY, 1986; Vol. 5.
18. For selected recent examples of alkyl radical addition to C=N bonds, see: (a) Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131-134.
19. (b) Friestad, G. K.; Qin, J. J. Am. Chem. Soc. 2001, 123, 9922-9923.
20. (c) Halland, N.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295.
21. (d) Ryu, I.; Kuriyama, H.; Minakata, S.; Komatsu, M.; Yoon, J.-Y.; Kim, S. J. Am. Chem. Soc. 1999, 121, 12190-12191. See also ref 3a-c.
22. (a) Mosca, R.; Fagnoni, M.; Mella, M.; Albini, A. Tetrahedron 2001, 57, 10319-10328.
23. (b) Kim, S.; Kim, N.; Chung, W.-J.; Cho, C. H. Synlett 2001, 937-940.
24. (c) Hirano, K.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 2457-2458.
25. (d) Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 613-615.
26. (e) Yoshimitsu, T.; Tsunoda, M.; Nagaoka, H. Chem. Commun. 1999, 1745.
27. (f) Alves, M. J.; Gilchrist, T. L.; Sousa, J. H. J. Chem. Soc., Perkin Trans. 1 1999, 1305-1310.
28. (g) Clark, A. J.; Rooke, S.; Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909-912.
29. (h) Ishida, A.; Sugita, D.; Itoh, Y.; Takamuku, S. J. Am. Chem. Soc. 1995, 117, 11687-11694.
30. (i) Citterio, A.; Filippini, L. Synthesis 1986, 6, 473.
31. (j) Fraser-Reid, B.; Anderson, R. C.; Hicks, D. R.; Walker, D. L. Can. J. Chem. 1977, 55, 3986-3995.
32. (k) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038.
33. Intramolecular nucleophilic addition of ether radical was nicely applied to the G ring formation of ciguatoxin by Hirama et al.: Hirama, M.; Oishi, T.; Uehara, H.; Inoue, M.; Maruyama, M.; Oguri, H.; Satake, M. Science 2001, 294, 1904-1907 and references therein.
34. Three methods, A-C, are described in this paper. A trace amount of air-oxygen seemed to enter the reaction flask through the connections of the apparatuses in Method A. Silicon grease on the connections prevented air invasion in Method B.
35. The structure of the major isomer was presented.
36. Generation of an alkyl radical by the autoxidation of trialkylborane is well-known and has been widely studied since Brown's report: (a) Brown, H. C.; Kabalka, G. W. J. Am. Chem. Soc. 1970, 92, 714-716. For recent examples for use of triethylborane-air as a radical initiator, see:
37. (b) Guindon, Y.; Prévest, M.; Mochirian, P.; Guérin B. Org. Lett. 2002, 4, 1019-1022.
38. (c) Kitagawa, O.; Yamada Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011-1013.
39. (d) Williams, A. L.; Grillo, T. A.; Comins, D. L. J. Org. Chem. 2002, 67, 1972-1973.
40. (e) Mima, K.; Ishihara, T.; Kuwahata, S.; Konno, T.; Yamanaka, H. Chem. Lett. 2002, 192-193.
41. (f) Mancheño, M. J.; Ramĩrez-Lõpez, P.; Gõmez-Gallego, M.; Sierra, M. A. Organometallics 2002, 21, 989-992.
42. The α-C-H bde of THF has been reported to be 385 kJ/mol. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493-532.
43. Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757-824.