Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes

Jelena Ćiraković, Tom G. Driver, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

As an alternative to the strongly reducing conditions necessary for the formation of silacyclopropanes, silylene transfer was developed as a mild, functional group tolerant method of silacyclopropanation. Complex silacyclopropanes were formed from functionalized alkenes using cyclohexane di-tert-butyl silacyclopropane, 1, as the source of t-Bu2Si. Di-tert-butyl silylene can be generated from 1 through the use of a catalytic amount of a metal salt. At -27 °C, silver triflate catalyzes the transfer of t-Bu2Si from 1 to mono- and disubstituted alkenes stereospecifically and diastereoselectively. In situ functionalization of silacyclopropanes with catalytic zinc bromide and methyl formate provides for an expedient one-flask synthesis of complex oxasilacyclopentanes from alkenes.

Original languageEnglish (US)
Pages (from-to)9370-9371
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number32
DOIs
StatePublished - Aug 14 2002

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Alkenes
Olefins
Metals
Cyclohexane
Functional groups
Silver
Zinc
Salts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes. / Ćiraković, Jelena; Driver, Tom G.; Woerpel, Keith.

In: Journal of the American Chemical Society, Vol. 124, No. 32, 14.08.2002, p. 9370-9371.

Research output: Contribution to journalArticle

Ćiraković, Jelena ; Driver, Tom G. ; Woerpel, Keith. / Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes. In: Journal of the American Chemical Society. 2002 ; Vol. 124, No. 32. pp. 9370-9371.
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