Synthesis of cyclic peroxides via enyne-RCM/Diels-Alder reaction sequence

Bulletin of the Korean Chemical Society

Volumn 25, Issue 9, 2004, Pages 1307-1308

  Yang, Young Keun ^a   Lee, Susie ^a   Tae, Jinsung ^a  

^a Yonsei University   (South Korea)

Author keywords

Cyclic hydroxylamines; Cyclic peroxides; Diels Alder reactions; Enyne metathesis; Singlet oxygen

Indexed keywords

HYDROXYLAMINE; PEROXIDE; SINGLET OXYGEN;

ARTICLE; CHEMICAL BOND; CONJUGATION; DIELS ALDER REACTION; REACTION TIME; RING CLOSING METATHESIS; SYNTHESIS;

EID: 4644363090     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2004.25.9.1307     Document Type: Article

References (23)

1. For selected recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
2. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
3. For reviews on enyne-metathesis, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
4. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
5. (c) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
6. For recent examples of [4+2] cycloadditions of singlet oxygen, see: (a) Adam, W.; Bosio, S. G.; Degen, H.-G.; Krebs, O.; Stalke, D.; Schumacher, D. Eur. J. Org. Chem. 2002, 3944.
7. (b) Griesbeck, A. G.; Bartoschek, A. Chem. Commun. 2002, 1594.
8. (c) Jung, M.; Ham, J.; Song, J. Org. Lett. 2002, 4, 2763.
9. (a) Hioki, H.; Ooi, H.; Hamano, M.; Mimura, Y.; Yoshio, S.; Kodama, M.; Ohta, S.; Yanai, M.; Ikegami, S. Tetrahedron 2001, 57, 1235.
10. (b) Suzuki, M.; Oda, Y.; Hamanaka, N.; Noyori, R. Heterocydes 1990, 30, 517.
11. (c) Mueller, P.; Rodriguez, D. Helv. Chim. Acta 1985, 68, 975.
12. (a) Atasoy, B.; Ozen, R. Tetrahedron 1997, 53, 13867.
13. (b) Suzuki, M.; Ohtake, H.; Kameya, Y.; Hamanaka, N.; Noyori, R. J. Org. Chem. 1989, 54, 5292.
14. (c) Mahindroo, V. K.; Singh, V.; Dev, S. Ind. J. Chem., Sect. B 1988, 27B, 1080.
15. (d) OShea, K. E.; Foote, C. S. J. Org. Chem. 1989, 54, 3475.
16. (e) Kohmoto, S.; Kasai, S.; Yamamoto, M.; Yamada, K. Chem. Lett. 1988, 1477.
17. (f) Harirchian, B.; Magnus, P. D. Synth. Commun. 1977, 7, 119.
18. (a) Yang, Y.-K.; Tae, J. Synlett 2003, 1043.
19. (b) Yang, Y.-K.; Tae, J. Synlett 2003, 2017.
20. (c) Tae, J.; Hahn, D.-W. Tetrahedron Lett. 2004, 45, 3757.
21. (a) Koide, K.; Finkelstein, Z. B.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398.
22. (b) Miyabe, H.; Yoshida, K.; Matsumura, A.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 567.
23. +: 258.1341; found: 258.1343.