Use of an Aminosilyllithium for the Diastereoselective Synthesis of Diphenyl Oxasilacyclopentane Acetals and Polyols

Jason M. Tenenbaum, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

(Equation presented) The conjugate addition reaction of a stable, in situ generated silyllithium gives a β-hydroxysilyl ester with high diastereoselectivity. Conversion of the β-hydroxysilyl ester to a β-fluorosilyl ester affords the precursor to the oxasilacyclopentane acetal in high yields under mild conditions. A hydride reduction and subsequent intramolecular silylation lead to the acetal in excellent yields. Finally, highly selective nucleophilic substitution affords oxasilacyclopentanes, which undergo a mild oxidation to afford 1,3-trans diols with high selectivity.

Original languageEnglish (US)
Pages (from-to)4325-4327
Number of pages3
JournalOrganic Letters
Volume5
Issue number23
DOIs
StatePublished - Nov 13 2003

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acetals
Acetals
esters
Esters
synthesis
Addition reactions
Hydrides
hydrides
Substitution reactions
selectivity
substitutes
Oxidation
oxidation
diphenyl
polyol

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Use of an Aminosilyllithium for the Diastereoselective Synthesis of Diphenyl Oxasilacyclopentane Acetals and Polyols. / Tenenbaum, Jason M.; Woerpel, Keith.

In: Organic Letters, Vol. 5, No. 23, 13.11.2003, p. 4325-4327.

Research output: Contribution to journalArticle

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