Abstract
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 language | German |
|---|---|
| Pages (from-to) | 1181-1186 |
| Number of pages | 6 |
| Journal | Chemische Berichte |
| Volume | 124 |
| Issue number | 5 |
| DOIs | |
| State | Published - 1991 |
Keywords
- Dipolar cycloaddition
- Ethers, cyclic
- Nitro olefins
- Stereoselective cyclizations