Stereocontrol in solid-phase radical reactions: Radical addition to oxime ether anchored to polymer support

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1443-1445

  Miyabe, Hideto ^a   Konishi, Chihiro ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000500365     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005771m     Document Type: Article

References (35)

1. For reviews, see: (a) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
2. (b) Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562.
3. (c) Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301.
4. (d) Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, 1996.
5. (a) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174.
6. (b) Miyabe, H.; Tanaka, H.; Naito, T. Tetrahedron Lett. 1999, 40, 8387.
7. 2 as a radical initiator have been reported. See: (a) Routledge, A.; Abell, C.; Balasubramanian, S. Synlett 1997, 61.
8. (b) Du, X.; Armstrong, R. W. J. Org. Chem. 1997, 62, 5678.
9. (c) Sibi, M. P.; Chandramouli, S. V. Tetrahedron Lett. 1997, 38, 8929.
10. (d) Du, X.; Armstrong, R. W. Tetrahedron Lett. 1998, 39, 2281.
11. (e) Berteina, S.; De Mesmaeker, A. Tetrahedron Lett. 1998, 39, 5759.
12. (f) Berteina, S.; Wendeborn, S.; De Mesmaeker, A. Synlett 1998, 1231.
13. (g) Watanabe, Y.; Ishikawa, S.; Takao, G.; Tour, T. Tetrahedron Lett. 1999, 40, 3411.
14. (h) Yim, A.-M.; Vidal, Y.; Viallefont, P.; Martinez, J. Tetrahedron Lett. 1999, 40, 4535.
15. (i) Caddick, S.; Hamza, D.; Wadman, S. N. Tetrahedron Lett. 1999, 40, 7285.
16. (j) Zhu, X.; Ganesan, A. J. Comb. Chem. 1999, 1, 157.
17. For reviews, see: (a) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293.
18. (b) Chem. Rev. 1997, 97, 347-510 (whole issue of No. 2).
19. (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643.
20. (a) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465.
21. (b) Miyabe, H.; Fujii, K.; Naito, T. Org. Lett. 1999, 1, 569.
22. Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335.
23. For related examples, see: (a) Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. Synlett 1999, 1148.
24. (b) Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189.
25. (c) Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780.
26. For our related example, see: (a) Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789.
27. (b) Miyabe, H.; Ushiro, C.; Ueda, M.; Yamakawa, K.; Naito, T. J. Org. Chem. 2000, 65, 176.
28. 2CCH=NOBn) and Wang resin. See ref 2a.
29. 3, 1:10, v/v).
30. Diether, R. K.; Datar, R. Can. J. Chem. 1993, 71, 814.
31. Moody, C. J.; Gallagher, P. T.; Lightfoot, A. P.; Slawin, A. M. Z. J. Org. Chem. 1999, 64, 4419.
32. Carboxypolystyrene and Wang resins purchased from Novabiochem were used in all experiments.
33. The screening of several methods for the cleavage of the resin under the basic reaction conditions did not show good results because of the competitive reactions such as removal of the sultam and the formation of unidentified products.
34. 1H NMR analysis.
35. 2Zn act multiply as a Lewis acid, a radical initiator, and a terminator. See refs 5, 7, and 8.