Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer

Margaret A. Greene, Michel Prévost, Joshua Tolopilo, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen-hydrogen bonds across the carbon-carbon double bonds.

Original languageEnglish (US)
Pages (from-to)12482-12484
Number of pages3
JournalJournal of the American Chemical Society
Volume134
Issue number30
DOIs
StatePublished - Aug 1 2012

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Alkenes
Aldehydes
Olefins
Carbon
Silanes
Silver
Hydrogen
Hydrogen bonds
Oxygen

ASJC Scopus subject areas

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

Cite this

Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer. / Greene, Margaret A.; Prévost, Michel; Tolopilo, Joshua; Woerpel, Keith.

In: Journal of the American Chemical Society, Vol. 134, No. 30, 01.08.2012, p. 12482-12484.

Research output: Contribution to journalArticle

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