Synthesis of isoxazolines and isoxazoles via generation of nitrile oxides from O-stannyl aldoximes
β Scribed by Moriya, Osamu; Takenaka, Hideo; Urata, Yoshikiyo; Endo, Takeshi
- Book ID
- 121493697
- Publisher
- The Royal Society of Chemistry
- Year
- 1991
- Tongue
- English
- Weight
- 191 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0022-4936
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π SIMILAR VOLUMES
Treatment of aldoximes 1 with Magtrieve TM (CrO 2 ) in presence of dipolarophile 3 or 4, furnished a variety of isoxazolines 5a-u and isoxazoles 6a-q as 1,3-dipolar cycloaddition (1,3-DC) products (38 examples; 63-90% isolated yields). In situ formation of a nitrile oxide intermediate was confirmed
An efficient way to construct a library of isoxazoles and isoxazolines was developed by solution-phase 1,3-dipolar cycloaddition reaction of nitrile oxides with olefins and alkynes followed by precipitation of the products as HCl salts.