Iron Porphyrins and Iron Salens as Highly Enantioselective Catalysts for the Ring-Expansion Reaction of Epoxides to Tetrahydrofurans

Ulutürk M., Göllü M., TİLKİ T., Ertürk E.

Organic Letters, vol.27, no.12, pp.3083-3088, 2025 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 12
  • Publication Date: 2025
  • Doi Number: 10.1021/acs.orglett.5c00767
  • Journal Name: Organic Letters
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, MEDLINE, Nature Index
  • Page Numbers: pp.3083-3088
  • Middle East Technical University Affiliated: Yes

Abstract

Iron porphyrins have been found to be efficient catalysts for the ring-expansion reaction of epoxides with alkenes to give the corresponding tetrahydrofurans; very low loadings (down to 1 mol %) are sufficient to achieve high yields (up to 98%). Additionally, an iron(III) salen complex based on the axially chiral 1,1-binaphthalene backbone has been shown to catalyze the reaction with high enantioselectivity (e.g., 92% ee for calyxolane A).