Volume 29, Issue 31
Heterocyclic Compounds
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ChemInform Abstract: An Efficient and Stereoselective Conversion of Lactones to Substituted Cyclic Ethers.

H. YODA

H. YODA

Dep. Mol. Sci., Fac. Eng., Shizuoka Univ., Hamamatsu, Shizuoka 432, Japan

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M. MIZUTANI

M. MIZUTANI

Dep. Mol. Sci., Fac. Eng., Shizuoka Univ., Hamamatsu, Shizuoka 432, Japan

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K. TAKABE

K. TAKABE

Dep. Mol. Sci., Fac. Eng., Shizuoka Univ., Hamamatsu, Shizuoka 432, Japan

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First published: 20 June 2010

Abstract

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ChemInform Abstract

Cerium(III) chloride assisted addition of Grignard reagents to lactones and following BF3×OEt2 mediated deoxygenation of the resulting hemiketals [cf. (III)] with triethylsilane provides a general route to cyclic ethers. The process is also effective for the diastereoselective formation of cyclic ethers derived from monosubstituted tetrahydrofuranones.

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