719301-88-9Relevant articles and documents
Highly diastereoselective 7-endo radical cyclization of ethyl α-methylene-γ-(bromomethyl)dimethylsiloxycarboxylates
Nagano, Hajime,Hara, Saori
, p. 4329 - 4332 (2007/10/03)
The 7-endo radical cyclization of (bromomethyl)dimethylsilyl ethers derived from ethyl γ-hydroxy-α-methylenecarboxylates bearing a bulky γ-substituent such as isopropyl, cyclohexyl, and tert-butyl groups in tetrahydrofuran gave preferentially cyclic silyl ethers bearing the ethoxycarbonyl group anti to the γ-substituents in high yields. Treatment of the cyclic silyl ethers with silica gel gave acyclic ethyl γ-hydroxy-α-[2-(hydroxydimethylsilyl)ethyl]carboxylates. The reduction of the cyclization products with DIBAL followed by Tamao oxidation gave the corresponding acyclic triols.