Jul 4, 2013
Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction
Beilstein Journal of Organic Chemistry
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- Volume
- 9
- Number
- First page
- 1326
- Last page
- 1332
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.3762/bjoc.9.149
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. © 2013 Miyazaki et al.
- Link information
- ID information
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- DOI : 10.3762/bjoc.9.149
- ISSN : 1860-5397
- SCOPUS ID : 84880865675
- Web of Science ID : WOS:000321301800001