Utilization of 1-Oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols

Sharon A. Powell, Jason M. Tenenbaum, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

We have developed a route for the stereoselective synthesis of 1-oxa-2,2-(dimesityl)silacyclopentane acetals, intermediates in the synthesis of highly functionalized 1,3-diols. This route involves a diastereoselective conjugate addition reaction of a hydrosilyl anion, a subsequent diastereoselective enolate alkylation, and a fluoride-catalyzed intramolecular hydrosilylation reaction to afford the oxasilacyclopentane acetal. A highly selective nucleophilic substitution reaction, followed by oxidation of the C-Si bond, leads to the desired polyol.

Original languageEnglish (US)
Pages (from-to)12648-12649
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number43
DOIs
StatePublished - Oct 30 2002

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Acetals
Polyols
Hydrosilylation
Addition reactions
Alkylation
Fluorides
Anions
Substitution reactions
Negative ions
Oxidation
polyol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Utilization of 1-Oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols. / Powell, Sharon A.; Tenenbaum, Jason M.; Woerpel, Keith.

In: Journal of the American Chemical Society, Vol. 124, No. 43, 30.10.2002, p. 12648-12649.

Research output: Contribution to journalArticle

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