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

Jelena Ćiraković; Tom G. Driver; K. A. Woerpel

doi:10.1021/jo0355505

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

Jelena Ćiraković, Tom G. Driver, K. A. Woerpel

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	4007-4012
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	69
Issue number	12
DOIs	https://doi.org/10.1021/jo0355505
State	Published - Jun 11 2004

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo0355505

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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.",

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T1 - Metal-catalyzed di-tert-butylsilylene transfer

T2 - Synthesis and reactivity of silacyclopropanes

AU - Ćiraković, Jelena

AU - Driver, Tom G.

AU - Woerpel, K. A.

PY - 2004/6/11

Y1 - 2004/6/11

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AB - 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.

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

Abstract

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