An α-alkylation/reduction of ketones via radical cyclizations of β-chloroethylsilyl enol ethers

Article abstract of DOI:10.1016/0040-4039(90)80008-A

β-Chloroethyldimethylsilyl enol ether derivatives of five ketones were allowed to react with tributylstannane in the presence of AIBN to yield the products of 'reductive α-alkylation', 1-oxa-2-silacyclohexanes, plus ethyldimethylsilyl enol ether byproducts from direct reduction. The unstable oxasilacyclohexanes were treated with methyllithium to yield, upon workup, γ-(trimethylsilyl) alcohols.