Metal-catalyzed di-tert-butylsilylene transfer: Synthesis and reactivity of silacyclopropanes

Jelena Ćiraković, Tom G. Driver, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Metal-catalyzed di-tert-butylsilylene transfer was developed as a mild, operationally simple, functional-group-tolerant method for silacyclopropane formation. Di-tert-butylsilylene was transferred from cyclohexene silacyclopropane 1 to an alkene through the use of a metal salt. Silacyclopropanation occurred at temperatures as low as -27°C when AgOTf or AgOC(O)CF3 were used as catalysts. Complex silacyclopropanes were formed stereospecifically and diastereoselectively from functionalized alkenes. Silacyclopropanes reacted with various carbonyl compounds, including aldehydes, ketones, formate esters, and formamides, in an overall process that efficiently converts alkenes into oxasilacyclopentanes with defined stereochemistry.

Original languageEnglish (US)
Pages (from-to)4007-4012
Number of pages6
JournalJournal of Organic Chemistry
Volume69
Issue number12
DOIs
StatePublished - Jun 11 2004

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Alkenes
Metals
Formic Acid Esters
Formamides
Carbonyl compounds
Stereochemistry
Ketones
Aldehydes
Functional groups
Salts
Catalysts
di-tert-butylsilylene
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Metal-catalyzed di-tert-butylsilylene transfer : Synthesis and reactivity of silacyclopropanes. / Ćiraković, Jelena; Driver, Tom G.; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 69, No. 12, 11.06.2004, p. 4007-4012.

Research output: Contribution to journalArticle

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