Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers

Christopher T. Avetta*, Leah C. Konkol, Carla N. Taylor, Karen C. Dugan, Charlotte L. Stern, Regan James Thomson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

46 Scopus citations

Abstract

(Chemical Equation Presented) Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.

Original languageEnglish (US)
Pages (from-to)5621-5624
Number of pages4
JournalOrganic Letters
Volume10
Issue number24
DOIs
StatePublished - Dec 1 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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