The stereochemistry of electrolysis and samarium diiodide-induced cyclization between carbonyl and enone system in inter- and intramolecular coupling

Heterocycles

Volumn 72, Issue , 2007, Pages 517-528

  Sono, Masakazu ^a   Shoji, Tsutomu ^a   Tamaki, Tatsuya ^a   Kishi, Satoko ^a   Tori, Motoo ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547830797     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-s(k)45     Document Type: Article

References (23)

1. Shono T. Electroorganic Synthesis (1991), Academic Press, London
2. Little R.D. Chem. Rev. 96 (1996) 93
3. Molander G.A. Chem. Rev. 92 (1992) 29
4. Molander G.A., and Harris C.R. Chem. Rev. 96 (1996) 307
5. Otsubo K., Inanaga J., and Yamaguchi M. Tetrahedron Lett. 27 (1986) 5763
6. Sono M., Nakashiba Y., Nakashima K., and Tori M. J. Org. Chem. 65 (2000) 3099
7. Sono M., Hashimoto A., Nakashima T., and Tori M. Tetrahderon Lett. 41 (2000) 5115
8. Sono M., Nakashiba Y., Nakashima K., Takaoka S., and Tori M. Heterocycles 54 (2001) 101
9. Sono M., Onishi S., and Tori M. Tetrahedron 59 (2003) 3385
10. 3 214.1569. {A figure is presented}
11. Ashby E.C., and Laemmle J.T. Chem. Rev. 75 (1975) 521
12. Maruoka K., Itoh T., Sakurai M., Nonoshita K., and Yamamoto H. J. Am. Chem. Soc. 110 (1998) 3588
13. The stereochemistry of compounds 5 and 6 was determined by NOESY spectra. The selected correlations were shown here. {A figure is presented}
14. 2 214.1933. {A figure is presented}
15. Curran D.P., Porter N.A., and Giese B. Stereochemistry of Radical Reactions (1996), VCH, Weinheim
16. Damm W., Giese B., Hartung J., Hasskerl T., Houk K.N., Hüter O., and Zipse H. J. Am. Chem. Soc. 114 (1992) 4067
17. 2-induced cyclization was discussed in ref. 5.
18. Compound 20 was prepared from 3-methylcyclopent-2-en-l-one in three steps (see Experimental). {A figure is presented}
19. The stereochemistry of 21 was established by NOESY spectrum. {A figure is presented}
20. Compound 22 was prepared from 3-methylcyclohex-2-en-l-one in three steps (see Experimental). {A figure is presented}
21. The stereochemistry of 23 was established by NOESY spectrum. {A figure is presented}
22. Compound 24 was prepared from 3-methylcyclopent-2-en-l-one in two steps (see Experimental). {A figure is presented}
23. The stereochemistry of compounds 25 and 26 was established by NOESY spectrum. {A figure is presented}