Stereoselective synthesis of tetrahydropyran-4-ones from dioxinones catalyzed by scandium(III) triflate

William J. Morris, Daniel W. Custar, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

46 Scopus citations

Abstract

(Chemical Equation Presented) A scandium triflate catalyzed, diastereoselective cyclization between aldehydes and β-hydroxy dioxinones has been discovered. This process capitalizes on the untapped nucleophilicity of the embedded enol ether within the dioxinone core. The bicyclic compounds from the resulting cyclization can be isolated, or alternatively, alkoxide nucleophiles can be directly added. This in situ addition fragments the dioxinone rings and delivers the 3-carboxy-substituted tetrahydropyran-4-ones in good yields with high levels of diastereoselectivity.

Original languageEnglish (US)
Pages (from-to)1113-1116
Number of pages4
JournalOrganic Letters
Volume7
Issue number6
DOIs
StatePublished - Mar 17 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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