Conversion of Tellurol Esters to Enol Silyl Ethers of Acylsilanes

Torn Inoue, Nobuaki Kambe*, Ilhyong Ryu, Noboru Sonoda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Tellurol esters having an anion stabilizing group at the position α to the carbonyl, such as aryl-, (phenylthio)-, and (benzyloxy)ethanetelluroates, gave enol silyl ethers of the corresponding acylsilanes in good to excellent yields upon treatment with 2 equiv of nBuLi in the presence of chlorosilanes. This reaction was stereoselective, and Z-isomers were obtained as sole or major products from a variety of chlorosilanes, such as trimethyl-, triethyl-, dimethylphenyl-, and tert-butyldimethylsilyl chlorides. Control experiments revealed that the reaction comprises the following consecutive processes: (i) α-proton abstraction, (ii) chlorosilane-trapping, (iii) lithium-tellurium exchange, (iv) 1,2-silyl migration, and (v) chlorosilane-trapping. Intramolecular rearrangement of (α-siloxyvinyl)lithiums to lithium enolates (step iv) was very fast even at −105 °C, and the former could not be trapped intermolecularly either with acetic acid or with coexisting trimethylsilyl chloride.

Original languageEnglish
Pages (from-to)8209-8214
Number of pages6
JournalJournal of Organic Chemistry
Volume59
Issue number26
DOIs
StatePublished - 1 Dec 1994

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