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Paper | Regular issue | Vol 48, No. 4, 1998, pp.679-686
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8060
An Efficient and Stereoselective Conversion of Lactones to Substituted Cyclic Ethers

Hidemi Yoda,* Masato Mizutani, and Kunihiko Takabe

*Department of Molecular Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan


A general route to substituted cyclic ethers has been described by using nucleophilic addition of Grignard reagents to lactones in the presence of CeCl3 followed by the Lewis acid-induced deoxygenation of the corresponding hemiketals with Et3SiH. Stereoselective reduction of the 5-membered adducts to the disubstituted tetrahydrofurans has been also investigated.