Acetal-induced cleavage of carbon-carbon bond of MEM ethers of (E)-4-alkyl-1-trimethylsilyl-1-alken-4-ols providing ketones

Article abstract of DOI:10.1016/0040-4039(94)80026-X

Treatment of methoxyethoxymethyl (MEM) ether of (E)-4-hexyl-1-trimethylsilyl-1-decen-4-ol with titanium(IV) chloride at -78°C afforded 7-tridecanone in 92% yield under cleavage of carbon-carbon bond. The new method was applied to the conversion of epoxides into ketones.