Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction.
Bicyclodihydrosiloles were readily prepared from optically active enyne compounds by a radical cascade reaction triggered by tris(trimethylsilyl)silane ((Me3Si)3SiH). The reaction was initiated by the addition of a silyl radical to an α,β-unsaturated ester, forming an α-carbonyl radical that underwent radical cyclization to a terminal alkyne unit. The resulting vinyl radical attacked the silicon atom in an SHi manner to give dihydrosilole. The reaction preferentially formed trans isomers of bicyclosiloles with an approximately 7:3 to 9:1 selectivity.
Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Ube 755-8611, Japan.
Koichiro
K
Miyazaki
Yu
Y
Yamane
Ryuichiro
R
Yo
Hidemitsu
H
Uno
Akio
A
Kamimura
SHi reaction; bicyclodihydrosilole; free radical; radical cascade reaction; tris(trimethylsilyl)silane