Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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