Strained organosilacyclic compounds

Synthesis of anti-Bredt olefins and trans-dioxasilacyclooctenes

Michel Prévost, Joseph W. Ziller, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Insertions of silylenes into the allylic carbon-oxygen bond of vinyl epoxides was shown to generate 1,2-silaoxetanes. These intermediates undergo highly diastereoselective additions to aldehydes to form anti-Bredt olefins and trans-dioxasilacyclooctenes. Additions of electrophiles could be performed selectively on the outside face of these strained trans-cycloalkenes to provide valuable functionalized compounds.

Original languageEnglish (US)
Pages (from-to)9275-9281
Number of pages7
JournalDalton Transactions
Volume39
Issue number39
DOIs
StatePublished - Oct 21 2010

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Cycloparaffins
Epoxy Compounds
Alkenes
Aldehydes
Carbon
Oxygen

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Strained organosilacyclic compounds : Synthesis of anti-Bredt olefins and trans-dioxasilacyclooctenes. / Prévost, Michel; Ziller, Joseph W.; Woerpel, Keith.

In: Dalton Transactions, Vol. 39, No. 39, 21.10.2010, p. 9275-9281.

Research output: Contribution to journalArticle

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