Substrate encapsulation: An efficient strategy for the RCM synthesis of unsaturated ε-lactones

Emily B. Pentzer*, Tendai Gadzikwa, Sonbinh T. Nguyen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

(Chemical Equation Presented) A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the α,ω-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered β,γ- and γ,δ-unsaturated lactones in good yields.

Original languageEnglish (US)
Pages (from-to)5613-5615
Number of pages3
JournalOrganic Letters
Volume10
Issue number24
DOIs
StatePublished - 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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