Synthesis of silyloxy dienes by silylene transfer to divinyl ketones

Application to the asymmetric synthesis of substituted cyclohexanes

Christian C. Ventocilla, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Silver-catalyzed silylene transfer to divinyl ketones provided 2-silyloxy-1,3-dienes with control of stereochemistry and regioselectivity. The products participated in Diels-Alder reactions with electron-deficient alkenes and imines to form six-membered-ring products diastereoselectively. Cycloaddition reactions with alkenes bearing chiral auxiliaries provided access to chiral, nonracemic cyclohexenes. The methodology, therefore, represents a synthesis of diastereomerically and enantiomerically pure products in a single flask. The highly substituted cyclohexene products could be functionalized stereoselectively to provide cyclohexanols after oxidation of the carbon-silicon bond.

Original languageEnglish (US)
Pages (from-to)3277-3283
Number of pages7
JournalJournal of Organic Chemistry
Volume77
Issue number7
DOIs
StatePublished - Apr 6 2012

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Cyclohexanes
Alkenes
Ketones
Cyclohexenes
Bearings (structural)
Cyclohexanols
Regioselectivity
Stereochemistry
Imines
Cycloaddition
Silicon
Silver
Carbon
Oxidation
Electrons
1,3-butadiene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of silyloxy dienes by silylene transfer to divinyl ketones : Application to the asymmetric synthesis of substituted cyclohexanes. / Ventocilla, Christian C.; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 77, No. 7, 06.04.2012, p. 3277-3283.

Research output: Contribution to journalArticle

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