Cycloadditions, 47. A Route to Functionalized Cyclic Ethers by Intramolecular Cycloadditions of Unsaturated Nitro Ethers

Alfred Hassner, Wim Dehaen

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A convenient conversion of aldehydes via nitroolefins 2 into cyclic ethers 6 fused to an isoxazoline ring involves formation of unsaturated nitroalkyl ethers 4 and subsequent intramolecular cycloaddition of an in situ‐formed nitrile oxide olefin. The cyclization proceeds with stereoselective formation of trans over cis isomers in the tetrahydrofuran series and opposite stereoselectivity in the tetrahydropyran and hexahydrooxepine series, depending on the substituent R in the original nitro compound, thus providing access to stereoselectively functionalized cyclic ethers.

Original languageGerman
Pages (from-to)1181-1186
Number of pages6
JournalChemische Berichte
Issue number5
StatePublished - 1991


  • Dipolar cycloaddition
  • Ethers, cyclic
  • Nitro olefins
  • Stereoselective cyclizations

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