Tetrahedron Letters p. 8067 - 8070 (1995)
Update date:2022-08-02
Topics:
Okada, Kenji
Matsumoto, Kozo
Oshima, Koichiro
Utimoto, Kiitiro
Treatment of 3-methylene-1,1-diphenylsilacyclobutane (1a) with dihalo-methyllithium provided ring expanded 2-halo-4-methylenesilacyclopentane. Heating a mixture of 1a and carbonyl compound such as PhCHO or PhCOMe at reflux in 1,2-dichloroethane afforded 5-methylene-1,1-diphenyl-2-oxa-1-silacyclohexane which was converted into 3-methylene-1,5-alkanediol monomethyl ether upon treatment with dimethyl acetal in the presence of Lewis acid catalyst. Treatment of ketoaldehyde (PhCOCH2CH2CHO) with 1a under BF3 · OEt2 catalysis gave 3-methylene-1-phenyl-8-oxabicyclo[3.2.1]octane in one pot.
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