Formal [3+2] Cycloaddition Reactions of Electron-Rich Aryl Epoxides with Alkenes under Lewis Acid Catalysis Affording Tetrasubstituted Tetrahydrofurans

Molecules. 2020 Feb 6;25(3):692. doi: 10.3390/molecules25030692.

Abstract

We report on the regio- and stereoselective synthesis of tetrahydrofurans by reaction between epoxides and alkenes in the presence of a Lewis acid. This is an unprecedented formal [3+2] cycloaddition reaction between an epoxide and an alkene. The chemical reaction represents a very concise synthesis of tetrahydrofurans from accessible starting compounds.

Keywords: cycloaddition; epoxides; lignans.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cycloaddition Reaction / methods
  • Electrons
  • Epoxy Compounds / chemistry*
  • Furans / chemistry*
  • Lewis Acids / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Epoxy Compounds
  • Furans
  • Lewis Acids