Volume 20, Issue 22
Heterocyclic Compounds
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ChemInform Abstract: One-Pot Synthesis of α-Mono- and α,α-Disubstituted Cyclic Ethers from Lactones.

T. MUKAIYAMA

T. MUKAIYAMA

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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K. HOMMA

K. HOMMA

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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H. TAKENOSHITA

H. TAKENOSHITA

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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First published: May 30, 1989

Abstract

The lactones (I) are coupled with the ethyl silyl ketene acetal (II) in the presence of Lewis acids and the silyl-substituted nucleophiles (III) to produce the ethoxycarbonylmethyloxacycloalkanes (IV).

ChemInform Abstract

The lactones (I) are coupled with the ethyl silyl ketene acetal (II) in the presence of Lewis acids and the silyl-substituted nucleophiles (III) to produce the ethoxycarbonylmethyloxacycloalkanes (IV). Various catalytic systems are tested. Optimum results are obtained using trityl hexachloroantimonate or a mixture of antimony pentachloride, chlorotrimethylsilane, and tin(II) iodide.

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