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Beilstein J Org Chem. 2013 Jul 4;9:1326-32. doi: 10.3762/bjoc.9.149. eCollection 2013.

Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction.

Author information

  • 1Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Ube 755-8611, Japan.

Abstract

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.

KEYWORDS:

SHi reaction; bicyclodihydrosilole; free radical; radical cascade reaction; tris(trimethylsilyl)silane

PMID:
23946827
[PubMed]
PMCID:
PMC3740799
Free PMC Article

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