Radical cascade reaction with 1,4-dienes and 1,4-enynes using 2-(iodomethyl)cyclopropane-1,1-dicarboxylate as a homoallyl radical precursor: One-step synthesis of bicyclo[3.3.0]octane derivatives

Organic Letters

Volumn 4, Issue 6, 2002, Pages 1011-1013

  Kitagawa, Osamu ^a   Yamada, Yoichiro ^a   Sugawara, Atsushi ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

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EID: 0000320850     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025583r     Document Type: Article

References (24)

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17. 3 brought about a considerable decrease in the chemical yield.
18. 2, NaH, t-BuOK), an increase in the chemical yield of 3b was not observed.
19. Riemenschneider, K.; Bartels, H. M.; Dornow, R.; Dreschel-Grau, E.; Eichel, W.; Luthe, H.; Matter, Y. M.; Michaelis, W.; Boldt, P. J. Org. Chem. 1987, 52, 205.
20. For reviews in relation to radical cascade reactions, see: (a) Jasperse, C. P.; Curran D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
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23. For recent examples in relation to the synthesis of polycyclic compounds through a radical cascade reaction which is started from intermolecular addition, see: (a) Jung, M. E.; Rayle, H. L. J. Org. Chem. 1997, 62, 4601.
24. (b) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. These reactions using a cyclic homoallyl radical involve two consecutive C-C bond formations.