Formation and utility of oxasilacyclopentenes derived from functionalized alkynes

Timothy B. Clark, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Oxasilacyclopentenes were shown to be synthetically useful masked allylic alcohols constructed in high yields and regioselectivities from terminal and internal alkynes. Several functional groups were shown to be tolerated utilizing silver-catalyzed silacyclopropenation of alkynes. In situ insertion of various carbonyl compounds into silacyclopropenes afforded regioselective formation of oxasilacyclopentenes. Elaboration of the oxasilacyclopentenes displayed the synthetic utility of these substrates. Both diastereoselective hydrogenation and Diels-Alder reactions utilizing the vinylsilane functionality demonstrated the reactivity and synthetic utility of oxasilacyclopentenes.

Original languageEnglish (US)
Pages (from-to)9522-9523
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number31
DOIs
StatePublished - Aug 11 2004

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Carbonyl compounds
Regioselectivity
Alkynes
Functional groups
Hydrogenation
Silver
Alcohols
Cycloaddition Reaction
Substrates
vinylsilane
allyl alcohol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Formation and utility of oxasilacyclopentenes derived from functionalized alkynes. / Clark, Timothy B.; Woerpel, Keith.

In: Journal of the American Chemical Society, Vol. 126, No. 31, 11.08.2004, p. 9522-9523.

Research output: Contribution to journalArticle

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