Tetrahedron Letters p. 3571 - 3574 (2016)
Update date:2022-08-05
Topics:
Kinoshita, Hidenori
Fukumoto, Hiroki
Tohjima, Takayuki
Miura, Katsukiyo
The reaction of o-[2-(trimethylsilyl)ethynyl]benzyl methyl ethers with diisobutylaluminum hydride (DIBAL-H) gave 2-(trimethylsilyl)indenes in good yields. This cyclization proceeds by regio- and stereoselective hydroalumination of the alkyne moiety followed by intramolecular nucleophilic substitution. o-[2-(Trimethylsilyl)ethynyl]phenylsilyl methyl ethers also underwent the DIBAL-H promoted-cyclization to be converted into 2-(trimethylsilyl)benzosiloles in good yields. This approach provides straightforward and efficient way to construct benzosiloles from readily available organosilanes.
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