Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction

Autor: Koichiro Miyazaki, Yu Yamane, Ryuichiro Yo, Hidemitsu Uno, Akio Kamimura
Jazyk: angličtina
Rok vydání: 2013
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 9, Iss 1, Pp 1326-1332 (2013)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.9.149
Popis: 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.
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