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

Osamu Kitagawa; Yoichiro Yamada; Atsushi Sugawara; Takeo Taguchi

doi:10.1021/ol025583r

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

Org Lett. 2002 Mar 21;4(6):1011-3. doi: 10.1021/ol025583r.

Authors

Osamu Kitagawa¹, Yoichiro Yamada, Atsushi Sugawara, Takeo Taguchi

Affiliation

¹ Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

PMID: 11893209
DOI: 10.1021/ol025583r

Abstract

[reaction: see text] Radical cascade reaction with various 1,4-dienes and 1,4-enynes using dimethyl 2-(iodomethyl)cyclopropane-1,1-dicarboxylate as a homoallyl radical precursor smoothly proceeds through an iodine atom transfer mechanism to give functionalized bicyclo[3.3.0]octane derivatives in good yields.